Relevant bibliographies by topics / Alcohols. Grignard reagents

Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Alcohols. Grignard reagents'

Author: Grafiati
Published: 4 June 2021
Last updated: 16 February 2022

Create a spot-on reference in APA, MLA, Chicago, Harvard, and other styles

Select a source type:

Consult the lists of relevant articles, books, theses, conference reports, and other scholarly sources on the topic 'Alcohols. Grignard reagents.'

Next to every source in the list of references, there is an 'Add to bibliography' button. Press on it, and we will generate automatically the bibliographic reference to the chosen work in the citation style you need: APA, MLA, Harvard, Chicago, Vancouver, etc.

You can also download the full text of the academic publication as pdf and read online its abstract whenever available in the metadata.

Journal articles on the topic "Alcohols. Grignard reagents"

1

Narayanaperumal, Senthil, Ricardo S. Schwab, Wystan K. O. Teixeira, and Danilo Yano de Albuquerque. "Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds." Synthesis 52, no. 13 (March 16, 2020): 1855–73. http://dx.doi.org/10.1055/s-0039-1690847.

Full text
Abstract:
Enantiomerically enriched diaryl, aryl heteroaryl, and dihetero­aryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion
APA, Harvard, Vancouver, ISO, and other styles
2

El-Aal, Abd, and Ali Khalaf. "Modern Friedel-Crafts chemistry: Part 36. Facile synthesis of some new pyrido[3,2,1-jk]carbazoles via Friedel-Crafts cyclialkylations." Journal of the Serbian Chemical Society 78, no. 5 (2013): 611–19. http://dx.doi.org/10.2298/jsc120520098a.

Full text
Abstract:
An efficient methodology for the synthesis of novel substituted pyrido[3,2,1-jk]carbazole via Friedel-Crafts cyclialkylations is reported. The methodology was realized by three-step protocol involved the addition of carbazole to 3-methylcrotononitrile. The resulted nitrile was hydrolyzed to desired ester, followed by addition of Grignard reagents to afford tertiary alcohols and/or reacted directly with different Grignard reagent to form the desired ketones. The later ketones were converted to both secondary and tertiary alcohols by reduction with LAH and addition of Grignard reagents respectively. These carbinols were cyclialkylated under Friedel-Crafts conditions catalyzed by AlCl3/CH3NO2, PTSA and PPA to give tri-and tetrasubstituted pyrido[3,2,1-jk]carbazole.
APA, Harvard, Vancouver, ISO, and other styles
3

Cai, Mingzhong, and Jun Xia. "A facile stereoselective synthesis of (E)-2,3-disubstituted allylic alcohols via hydromagnesiation of alkylarylacetylenes." Journal of Chemical Research 2005, no. 2 (February 2005): 121–22. http://dx.doi.org/10.3184/0308234054497155.

Full text
Abstract:
Hydromagnesiation of alkylarylacetylenes 1 in diethyl ether gave (E)-α-arylvinyl Grignard reagents 2, which reacted with aldehydes or ketones 3 to afford stereoselectively (E)-2,3-disubstituted allylic alcohols 4 in good yields.
APA, Harvard, Vancouver, ISO, and other styles
4

Cai, Mingzhong, Chunyun Peng, Hong Zhao, and Wenyan Hao. "A Stereoselective Synthesis of (E)-Allylic Alcohols Via the Hydromagnesiation of Alkynylsilanes." Journal of Chemical Research 2003, no. 5 (May 2003): 296–98. http://dx.doi.org/10.3184/030823403103173877.

Full text
Abstract:
Hydromagnesiation of alkynylsilanes 1 gives ( Z)-α-silylvinyl Grignard reagents 2, which are reacted with aldehydes or ketones to afford ( Z)-β-silyl allylic alcohols 3 in high yields; intermediates 3 can undergo the desilylation reaction in the presence of anhydrous KF to give ( E)-allylic alcohols 4 in good yields.
APA, Harvard, Vancouver, ISO, and other styles
5

Batchelor, Kevin J., W. Russell Bowman, Roy V. Davies, Michael H. Hockley, and David J. Wilkins. "Regioselective Addition of Grignard Reagents to Isoxazole-4,5-dicarboxylate Esters." Journal of Chemical Research 23, no. 7 (July 1999): 428–29. http://dx.doi.org/10.1177/174751989902300712.

Full text
Abstract:
Regioselective mono-addition of a range of Grignard reagents with the 5-esters of 3-methylisoxazole-4,5-diesters affords 5-keto derivatives instead of tertiary alcohols which is explained by the complexing ability of the isoxazole oxygen atom and by the electron withdrawing effect of the isoxazole ring.
APA, Harvard, Vancouver, ISO, and other styles
6

Ma, S., and Z. Lu. "Cu-Catalyzed Carbometallation of Propargylic Alcohols by Grignard Reagents." Synfacts 2006, no. 6 (June 2006): 0603. http://dx.doi.org/10.1055/s-2006-941772.

Full text
APA, Harvard, Vancouver, ISO, and other styles
7

Barrett, A., and T. Werner. "Simple Preparation of Esters from Grignard Reagents and Alcohols." Synfacts 2006, no. 8 (August 2006): 0826. http://dx.doi.org/10.1055/s-2006-942007.

Full text
APA, Harvard, Vancouver, ISO, and other styles
8

Moiseenkov, Alexander M., and Boris A. Czeskis. "Synthesis of some monoterpenols via cyclopropylcarbinyl rearrangement." Collection of Czechoslovak Chemical Communications 51, no. 6 (1986): 1316–22. http://dx.doi.org/10.1135/cccc19861316.

Full text
Abstract:
Condensation of appropriately substituted aldehydes and Grignard reagents leads to cyclopropyl alcohols V - VIII chromatographically separated in all cases into individual diastereoisomers. Perchloric acid catalyzed cyclopropylcarbinyl rearrangement of V - VIII (as a mixture of diastereoisomers or individual isomers) gives unsaturated monoterpenols IX - XII with high regio- and stereospecifity.
APA, Harvard, Vancouver, ISO, and other styles
9

Minnaard, Adriaan, and Beatriz Calvo. "Copper-Catalyzed Asymmetric 1,2-Addition of Grignard Reagents to 3-Acyl 2H-chromenes." Synlett 28, no. 19 (August 17, 2017): 2624–28. http://dx.doi.org/10.1055/s-0036-1588532.

Full text
Abstract:
Enones in which the carbon–carbon double bond is part of the pharmacologically important 2H-chromene (2H-1-benzopyran) nucleus undergo asymmetric copper-catalyzed 1,2-addition of Grignard reagents. High yields and enantiomeric excesses up to 84% are obtained and access to these novel enantio-enriched tertiary alcohols is provided.
APA, Harvard, Vancouver, ISO, and other styles
10

Kanno, Ken-ichiro, Yumi Aikawa, Yuka Niwayama, Misaki Ino, Kento Kawamura, and Soichiro Kyushin. "Stepwise Introduction of Different Substituents to α-Chloro-ω-hydrooligosilanes: Convenient Synthesis of Unsymmetrically Substituted Oligosilanes." Inorganics 6, no. 3 (September 18, 2018): 99. http://dx.doi.org/10.3390/inorganics6030099.

Full text
Abstract:
A series of unsymmetrically substituted oligosilanes were synthesized via stepwise introduction of different substituents to α-chloro-ω-hydrooligosilanes. The reactions of α-chloro-ω-hydrooligosilanes with organolithium or Grignard reagents gave hydrooligosilanes having various alkyl, alkenyl, alkynyl and aryl groups. Thus-obtained hydrooligosilanes were converted into alkoxyoligosilanes by ruthenium-catalyzed dehydrogenative alkoxylation with alcohols.
APA, Harvard, Vancouver, ISO, and other styles
More sources

Dissertations / Theses on the topic "Alcohols. Grignard reagents"

1

Neouchy, Zeïna. "Couplage croisé d’éthers d’énol méthyliques par activation de liaisons C(sp2)-OCH3 catalysée par le nickel et Synthèse d’amines α-trifluorométhylées acycliques optiquement activespar réarrangement de β-aminoalcools α-trifluorométhylés." Thesis, Paris Sciences et Lettres (ComUE), 2018. http://www.theses.fr/2018PSLET016.

Full text
Abstract:
En chimie organique, le développement de méthodes de synthèse robustes et respectueuses de l’environnement a toujours été un défi. De plus, en chimie médicinale, la mise au point de méthodes de synthèse de synthons fluorés de haute valeur ajoutée sont importantes pour avoir accès à des composés bioactifs. Dans ce manuscrit, nous présentons des méthodes efficaces et faciles à mettre en œuvre pour la formation de liaisons carbone-carbone catalysée par le nickel et la formation de liaisons carbone hétéroatome par un réarrangement de β aminoalcools α-trifluorométhylés.Nous avons montré que le couplage croisé entre un éther d’énol méthylique et un réactif de Grignard pouvait être catalysé par un système simple à base de Ni(OAc)2/(O)PPh3 dans des conditions douces (40°C) via l’insertion du nickel dans la liaison C-OMe. Cette méthode a été appliquée à la synthèse d’un composé antitumoral, le DMU-212.La synthèse d’amines α-trifluorométhylées linéaires énantioenrichies a été réalisée selon une réaction de réarrangement régiosélectif de β-aminoalcools α-trifluorométhylés en se basant sur une stratégie établie dans le laboratoire via un intermédiaire aziridinium. Nous avons montré que les produits obtenus pouvaient être engagés dans des réactions de post-fonctionnalisation
In organic chemistry, the development of robust and sustainable synthetic methods has always been a challenge. Moreover, in medicinal chemistry, the development of fluorinated building blocks synthetic methods with high value is important to access bioactive compounds. In this manuscript, we report efficient and easy to carry methods for the formation of carbon-carbon bonds catalyzed by nickel and the formation of carbon-heteroatom bonds by a rearrangement of α-trifluoromethyl-β aminoalcools.We demonstrated that it is possible to perform a cross-coupling reaction of an alkenyl methy ether with a Grignard reagent using a simple catalytic system based on Ni(OAc)2/(O)PPh3 under mild conditions (40°C) via the insertion of nickel into C-OMe bond. This method has been applied to the synthesis of an antitumoral agent, DMU-212.The synthesis of enantioenriched linear α-trifluoromethylamine derivatives is reported consisting in a rearrangement of α-trifluoromethyl-β aminoalcool based on an established strategy in our group via an aziridinium intermediate. We have shown that the synthesized compounds can be involved in post-functionalization reactions
APA, Harvard, Vancouver, ISO, and other styles
2

Alvarez, Gonzalez Eleuterio. "Substitution d'ethers et d'alcools allyliques par differents nucleophiles en presence de complexes de nickel(0) : synthese stereoselective des dienes-1,4 a partir des sulfones dieniques avec le chlorure d'isopropylmagnesium en presence de sels de." Paris 6, 1987. http://www.theses.fr/1987PA066064.

Full text
APA, Harvard, Vancouver, ISO, and other styles

Book chapters on the topic "Alcohols. Grignard reagents"

1

Parsons, A. F. "Using Grignard Reagents." In Alcohols, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00143.

Full text
APA, Harvard, Vancouver, ISO, and other styles
2

Hodgson, D. M., and P. G. Humphreys. "Using Grignard Reagents." In Alcohols, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00532.

Full text
APA, Harvard, Vancouver, ISO, and other styles
3

Hodgson, D. M., and P. G. Humphreys. "Addition of Grignard Reagents." In Alcohols, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00527.

Full text
APA, Harvard, Vancouver, ISO, and other styles
4

Frost, C. G., and J. Le Nôtre. "Enantioselective Additions of Grignard Reagents." In Alcohols, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00205.

Full text
APA, Harvard, Vancouver, ISO, and other styles
5

Scott, P. J. H., and P. G. Steel. "Reactions of α-Halo Epoxides with Grignard Reagents." In Alcohols, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-036-00385.

Full text
APA, Harvard, Vancouver, ISO, and other styles
6

Taber, Douglass. "Enantioselective Assembly of Alkylated Stereogenic Centers." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0037.

Full text
Abstract:
Oxygenated secondary stereogenic centers are readily available. There is a limited range of carbon nucleophiles that will displace a secondary leaving group in high yield with clean inversion. Teruaki Mukaiyama of the Kitasato Institute has described (Chem. Lett. 2007, 36, 2) an elegant addition to this list. Phosphinites such as 1 are easily prepared from the corresponding alcohols. Quinone oxidation in the presence of a nucleophile led via efficient displacement to the coupled product 2. The sulfone could be reduced with SmI2 to give 3. Enantioselective reduction of trisubstituted alkenes is also a powerful method for establishing alkylated stereogenic centers. Juan C. Carretero of the Universidad Autonoma de Madrid has found (Angew. Chem. Int. Ed. 2007, 46, 3329) that the enantioselective reduction of unsaturated pyridyl sulfones such as 4 was directed by the sulfone, so the other geometric isomer of 4 gave the opposite enantiomer of 5. The protected hydroxy sulfone 5 is a versatile chiral building block. Samuel H. Gellman of the University of Wisconsin has reported (J. Am. Chem. Soc. 2007, 129, 6050) an improved procedure for the aminomethylation of aldehydes. L-Proline-catalyzed condensation with the matched α-methyl benzylamine derivavative 7 gave the aldehyde, which was immediately reduced to the alcohol 8 to avoid racemization. The amino alcohol 8 was easily separated in diastereomerically-pure form. In the past, aldehydes have been efficiently α-alkylated using two-electron chemistry. David W. C. Macmillan of Princeton University has developed (Science 2007, 316, 582; J. Am. Chem. Soc. 2007, 129, 7004) a one-electron alternative. The organocatalyst 9 formed an imine with the aldehyde. One-electron oxidation led to an α-radical, which was trapped by the allyl silane (or, not pictured, a silyl enol ether) leading to the α-alkylated aldehyde 10. This is mechnistically related to the work reported independently by Mukund P. Sibi (J. Am. Chem. Soc. 2007, 129, 4124; OHL Feb. 11, 2008) on one-electron α-oxygenation of aldehydes. Secondary alkylated centers can also be prepared by SN2’ alkylation of prochiral substrates such as 11. Ben L. Feringa of the University of Groningen has shown (J. Org. Chem. 2007, 72, 2558) that the displacement proceeded with high ee even with conventional Grignard reagents.
APA, Harvard, Vancouver, ISO, and other styles
7

Taber, Douglass. "New Methods for Carbon-Carbon Bond Construction." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0017.

Full text
Abstract:
Mohammad Navid Soltani Rad of Shiraz University of Technology has shown (Tetrahedron Lett. 2007, 48, 6779) that with tosylimidazole (TsIm) activation in the presence of NaCN, primary, secondary and tertiary alcohols are converted into the corresponding nitriles. Gregory C. Fu of MIT has devised (J. Am. Chem. Soc. 2007, 129, 9602) a Ni catalyst that mediated the coupling of sp3-hybridized halides such as 3 with sp3-hybridized organoboranes such as 4, to give 5. Usually, carbanions with good leaving groups in the beta position do not couple efficiently, but just eliminate. Scott D. Rychnovsky of the University of California, Irvine has found (Organic Lett . 2007, 9, 4757) that initial protection of 6 as the alkoxide allowed smooth reduction of the sulfide and addition of the derived alkyl lithium to the amide 7 to give 8. Doubly-activated Michael acceptors such as 11 are often too unstable to isolate. J. S. Yadav of the Indian Institute of Chemical Technology, Hyderabad has shown (Tetrahedron Lett. 2007, 48, 7546) that Baylis-Hillman adducts such as 9 can be oxidized in situ, with concomitant Sakurai addition to give 12. Rather than use the usual Li or Na or K enolate, Don M. Coltart of Duke University has found (Organic Lett. 2007, 9, 4139) that ketones such as 13 will condense with amides such as 14 to give the diketone 15 on exposure to MgBr2. OEt2 and i -Pr2 NEt. Simultaneously, Gérard Cahiez of the Université de Cergy (Organic Lett. 2007, 9, 3253) and Janine Cossy of ESPCI Paris (Angew. Chem. Int. Ed. 2007, 46, 6521) reported that Fe salts will catalyze the coupling of sp2 -hybridized Grignard reagents such as 17 with alkyl halides. John Montgomery of the University of Michigan has described (J. Am. Chem. Soc. 2007, 129, 9568) the Ni-mediated regio- and enantioselective addition of an alkynes 20 to an aldehyde 19 to give the allylic alcohol 21. In a third example of sp2 - sp3 coupling, Troels Skrydstrup of the University of Aarhus has established (J. Org. Chem. 2007, 72, 6464) that Negishi coupling with alkenyl phosponates such as 23 proceeded efficiently.
APA, Harvard, Vancouver, ISO, and other styles
8

Taber, Douglass F. "Best Synthetic Methods: C-C Bond Construction." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0022.

Full text
Abstract:
Nobuaki Kambe of Osaka University found (Tetrahedron Lett. 2009, 50, 5644) that with a Ni catalyst, Grignard reagents coupled preferentially with primary alkyl iodides, even in the presence of the usually reactive ketone. Maurice Santelli of the Université d’Aix-Marseille devised (Tetrahedron Lett. 2009, 50, 5238) a protocol for the conversion of a ketal 4 to the doubly homologated product 6. Brian T. Gregg of AMRI established (Tetrahedron Lett. 2009, 50, 3978; Tetrahedron Lett. 2009, 50, 7070) a procedure for the homologation of a nitrile 7 to the amine 9. Replacement of the NaBH4 with a second Grignard reagent led to the α-quaternary amine (not shown). Toshiaki Murai of Gifu University independently developed (J. Org. Chem. 2009, 74, 5703) a protocol for coupling two Grignard reagents with the linchpin reagent 11 to give the amine 12. Laurel L. Schafer of the University of British Columbia demonstrated (Angew. Chem. Int. Ed. 2009, 48, 8361) Ta-catalyzed intramolecular addition of a methyl amine 14 to the terminal alkene 13 to give 15. Jason S. Kingsbury of Boston College extended (Organic Lett. 2009, 11, 3202) the Roskamp protocol to unstable diazo alkanes such as 17, to give 18. Katsukiyo Miura of Saitama University found (Organic Lett. 2009, 11, 5066) that Pt catalyzed the branched addition of a terminal alkenyl silane 19 to an aldehyde 16 to give the branched adduct 20. Silanes such as 19 are readily prepared directly from the corresponding terminal alkene. Kálmán J. Szabó of Stockholm University observed (J. Org. Chem. 2009, 74, 5695) that the allyl boronate derived from the allylic alcohol 21 could add to the aldehyde 23 to give, depending on the solvent, either the branched product 24 or the linear product 25. The Wittig reaction is a major producer of by-product waste in chemical synthesis. Yong Tang of the Shanghai Institute of Organic Chemistry found (J. Org. Chem. 2007, 72, 6628) that Ph3As could serve catalytically in the condensation of 26 with an aldehyde. Christopher J. O’Brien of the University of Texas at Arlington and Gregory A. Chass of the University of Wales described (Angew. Chem. Int. Ed. 2009, 48, 6836) a related procedure using a cyclic phosphine.
APA, Harvard, Vancouver, ISO, and other styles
9

Taber, Douglass F. "New Methods for C-C Bond Construction." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0023.

Full text
Abstract:
Luigino Troisi of the University of Salento found (Tetrahedron Lett. 2010, 51, 371) that a variety of primary and secondary amines could be coupled with a benzylic halide 1 under carbonylating conditions. Ilhyong Ryu of Osaka Prefecture University showed (Organic Lett. 2010, 12, 1548) that under reducing conditions, an iodide 3 coupled with CO to give the primary alcohol. Felicia A. Etzkorn of Virginia Tech observed (Organic Lett. 2010, 12, 696) that under Hg hydrolysis conditions, the orthothioester derived from 5 coupled with 6 to give 7. Yasuharu Yoshimi of the University of Fukui and Minoru Hatanaka of Iwate Medical University devised (Tetrahedron Lett. 2010, 51, 2332) conditions for the decarboxylative addition of the acid 8 to 9 to give 10. Yong-Min Liang and Xiaojun Yao of Lanzhou University and Chao-Jun Li of McGill University described (J. Org. Chem. 2010, 75, 783) a related procedure with α-amino acids. Yasutaka Ishii of Kansai University established (J. Am. Chem. Soc. 2010, 132, 2536) that t -butyl acetate 12 was an effective partner for the Ir-mediated oxidation-coupling-reduction of an alcohol 11. He used (J. Org. Chem. 2010, 75, 1803) a similar protocol to condense acetone with the diol 14, to give the long-chain diketone 16. The formation of allylic Grignard reagents can be inefficient because the excess reactive halide tends to couple with the Grignard reagent as it forms. Brandon L. Ashfeld of the University of Notre Dame found (Tetrahedron Lett. 2010, 51, 2427) a simple solution to this problem: inclusion of a catalytic amount of the inexpensive Cp2 TiCl2 to mediate the addition of 18 to 17. Brian T. Connell of Texas A&M University demonstrated (J. Am. Chem. Soc. 2010, 132, 7826) that with Mn, 21 could be added to 20. The acetate 21 is thus an easily prepared homoenolate equivalent. Note that although 21 is an E/Z mixture, the product 22 is cleanly Z. Gérard Cahiez of the Université de Paris 13 reported (Synlett 2010, 299) a detailed study of the Cu-catalyzed coupling of 24 with 23. Without supporting ligands, slow addition (syringe pump, 1 h) of 24 to 23 assured clean formation of 25. Manual slow addition (dropping funnel, 15 min) was not effective.
APA, Harvard, Vancouver, ISO, and other styles
10

Taber, Douglass. "The Betzer and Ardisson Synthesis of (+)-Discodermolide." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0085.

Full text
Abstract:
( + )-Discodermolide 3, a potent anticancer agent that works synergistically with taxol, may yet prove to be clinically effective. For the synthetic material to be affordable, a highly convergent synthesis is required. Jean-François Betzer and Janick Ardisson of the Université de Cergy- Pontoise have described (Angew. Chem. Int. Ed. 2007, 46, 1917) such a synthesis, coupling 1 and 2. A central feature of their approach was the repeated application of the inherently chiral secondary organometallic reagent 5. The first use of 5 was the addition to the aldehyde 4. The product 6 was ozonized, and the resulting aldehyde was carried on to the α, β-unsaturated ester. Exposure of the hydroxy ester to benzaldehyde under basic conditions delivered, by intramolecular Michael addition, the acetal 7. The next addition of the reagent 5 was to the aldehyde 10. The adduct 11 was deprotonated with t-BuLi to effect α-elimination, providing, after protection of the alcohol, the alkyne 12. Coupling of 12 with the amide 7 gave a ketone, enantioselective reduction of which under Itsuno-Corey conditions led, again after protection of the alcohol, to the alkyne 13. Oxidation followed by selective hydrogenation and iodine-tin exchange then completed the assembly of 1. Note that PtO2, not typically used for partial hydrogenation, was the catalyst of choice for this congested alkyne. The third application of the enantiomerically-pure reagent 5 was addition to the aldehyde that had been prepared by ozonolysis of 15. Advantage was then taken of another property of the alkenyl carbamate, Ni-mediated Grignard coupling, to form the next carbon-carbon bond with high geometric control. Deprotection of the diene 17 so prepared followed by iodination then completed the synthesis of 2. The convergent coupling of 1 with 2 was carried out under Suzuki conditions. Reduction of the iodide of 2 to the corresponding alkyl lithium followed by exchange with B-OMe-9-BBN gave an intermediate organoborane, that smoothly coupled with 1 under Pd catalysis to give 18.
APA, Harvard, Vancouver, ISO, and other styles
You might also be interested in the extended bibliographies on the topic 'Alcohols. Grignard reagents' for particular source types:
Journal articles
We offer discounts on all premium plans for authors whose works are included in thematic literature selections. Contact us to get a unique promo code!

To the bibliography