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Journal articles on the topic 'Chiral diene'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

ENDO, Akihisa, Masashi FUNATSU, and Yoshinobu INOUYE. "Diene Cyclization toward Chiral Acyliminium Ions." NIPPON KAGAKU KAISHI, no. 4 (1996): 416–18. http://dx.doi.org/10.1246/nikkashi.1996.416.

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2

Dong, Han-Qing, Ming-Hua Xu, Chen-Guo Feng, Xing-Wen Sun, and Guo-Qiang Lin. "Recent applications of chiral N-tert-butanesulfinyl imines, chiral diene ligands and chiral sulfur–olefin ligands in asymmetric synthesis." Organic Chemistry Frontiers 2, no. 1 (2015): 73–89. http://dx.doi.org/10.1039/c4qo00245h.

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3

Nagamoto, Midori, and Takahiro Nishimura. "Asymmetric Transformations under Iridium/Chiral Diene Catalysis." ACS Catalysis 7, no. 1 (2016): 833–47. http://dx.doi.org/10.1021/acscatal.6b02495.

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4

Bercich, Mark D., Richard C. Cambie, and Peter S. Rutledge. "Experiments Directed Towards the Synthesis of Anthracyclinones. XXXIV Hetero-Diels - Alder Reactions Using Chiral Boron and Titanium Reagents." Australian Journal of Chemistry 52, no. 9 (1999): 851. http://dx.doi.org/10.1071/ch98181.

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Reactions between benzaldehyde or o-anisaldehyde and a series of silyloxy dienes catalysed by the chiral acyl- oxyborane (CAB) complex (4) give high yields of enantioselective products from a Mukaiyama aldol rather than a hetero-Diels–Alder reaction. Attempts to effect a similar catalytic reaction with anthraquinone aldehydes were unsuccessful but use of 2 equiv. of the CAB complex (1) followed by cyclization promotes a formal hetero- Diels–Alder reaction between the aldehyde (7) and the diene (12) to give the dihydropyrone (24) in 45% yield and with a 79% e.e. in favour of the 2'R enantiomer.

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5

Sun, Yu-Tuo, Dong-Xing Zhu, Xiaofeng Rao, and Ming-Hua Xu. "The enantioselective construction of trifluoromethylated quaternary stereocenters via the Rh-catalyzed asymmetric dehydrated arylation of unprotected hemiaminals." Organic Chemistry Frontiers 7, no. 2 (2020): 340–44. http://dx.doi.org/10.1039/c9qo01203f.

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6

Min, Hyemin, Hiroyuki Miyamura, Tomohiro Yasukawa, and Shū Kobayashi. "Heterogeneous Rh and Rh/Ag bimetallic nanoparticle catalysts immobilized on chiral polymers." Chemical Science 10, no. 32 (2019): 7619–26. http://dx.doi.org/10.1039/c9sc02670c.

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We have developed novel heterogeneous chiral Rh and Rh/Ag NP catalysts immobilized on a chiral diene-containing polymer. The catalysts showed high activity in asymmetric reactions in both batch and flow systems.

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7

Yamaguchi, Hiroshi, Saburo Nakanishi, Nobuhiro Kihara та Toshikazu Takata. "Chiral Recognition with Crown Ethers Having Planar Chiral (η4-Diene)tricarbonyliron Moieties". Chemistry Letters 32, № 4 (2003): 410–11. http://dx.doi.org/10.1246/cl.2003.410.

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8

Shintani, Ryo, and Tamio Hayashi. "ChemInform Abstract: Chiral Diene Ligands for Asymmetric Catalysis." ChemInform 41, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.201026238.

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9

Du, H., and Z. Cao. "Rhodium Chiral Diene Catalyzed Asymmetric Arylation of Aldimines." Synfacts 2010, no. 09 (2010): 1038. http://dx.doi.org/10.1055/s-0030-1257992.

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10

Liu, Zuosheng, Jiong Lan, Yulin Li, Yacheng Xing, and Wen Cen. "Total Partial Synthesis of (3S, 6S)-(+)-3,7-Dimethyl-6-hydroxy-3-acetoxyocta-1,7-diene and (3S, 6S)-(-)-3,7-Dimethylocta-1,7-diene-3,6-diol from Geraniol." Journal of Chemical Research 23, no. 5 (1999): 324–25. http://dx.doi.org/10.1177/174751989902300514.

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The synthesis of (3 S, 6 S)-(+)-3,7-dimethyl-6-hydroxy-3-acetoxyocta-1,7-diene and (3 S, 6 S)-(-)-3,7-dimethylocta-1,7-diene-3,6-diol via the rearrangement of the chiral 2,3-epoxy alcohol, with the system Ph3P, pyridine, I2 and H2O, is described.

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11

Li, Ruikun, Zhongqing Wen, and Na Wu. "A nordehydroabietyl amide-containing chiral diene for rhodium-catalysed asymmetric arylation to nitroolefins." Organic & Biomolecular Chemistry 14, no. 47 (2016): 11080–84. http://dx.doi.org/10.1039/c6ob02202b.

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12

Xu, M. H., G. Q. Lin, C. G. Feng, Z. Q. Wang, and C. Shao. "Conjugate Additions Using a Water-Soluble Chiral Diene Ligand." Synfacts 2008, no. 11 (2008): 1181. http://dx.doi.org/10.1055/s-0028-1083435.

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13

Sawano, Takahiro, Pengfei Ji, Alexandra R. McIsaac, Zekai Lin, Carter W. Abney, and Wenbin Lin. "The first chiral diene-based metal–organic frameworks for highly enantioselective carbon–carbon bond formation reactions." Chemical Science 6, no. 12 (2015): 7163–68. http://dx.doi.org/10.1039/c5sc02100f.

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14

Martelli, Gianluca, and Diego Savoia. "A New Chiral Masked Form of Glyoxal Diimine." Collection of Czechoslovak Chemical Communications 68, no. 8 (2003): 1531–40. http://dx.doi.org/10.1135/cccc20031531.

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(3R,4R,5R,6R)-3,6-Diphenyl-N,N'-bis[(S)-1-phenylethyl]octa-1,7-diene-4,5-diamine, by treatment with organolithium reagents RLi in controlled experimental conditions, underwent rearrangement and/or substitution of one or two branched allyl(s) by the R group(s). Hence, this diene behaves as a masked form of the chiral glyoxal diimine from that it is prepared, allowing the preparation of C1-symmetric 1,2-disubstituted 1,2-diamines, which are generally not available by the direct addition of organometallic reagents to the diimine, and C2-symmetric 1,2-diamines with good diastereoselectivities.

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15

Roy, Iain D., Alan R. Burns, Graham Pattison, Boris Michel, Alexandra J. Parker, and Hon Wai Lam. "A second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes." Chem. Commun. 50, no. 22 (2014): 2865–68. http://dx.doi.org/10.1039/c4cc00340c.

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16

Northcott, Colleen J., and Zdenek Valenta. "A study of chiral induction in some diene additions catalyzed by chiral alkoxyaluminum dichlorides." Canadian Journal of Chemistry 65, no. 8 (1987): 1917–23. http://dx.doi.org/10.1139/v87-320.

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A reliable procedure for the preparation of the chiral Lewis acid catalysts, (−)-menthoxy- ((−)-1) and (−)-bornyloxy-aluminum dichloride ((−)-2), has been established for the study of diene additions. The geometry of conformationally mobile α,β-unsaturated carbonyl compounds complexed with these catalysts has been probed using the α-methylene ketones 3 and 4 and 2,6-dimethyl-1,4-benzoquinone 5 as dienophiles of fixed geometry. The addition of the first two to cyclopentadiene and (−)-1 yields exo and endo adducts that exhibit a range of 28–54% enantiomeric excess (ee); with 5, only the endo iso

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17

Zhou, Bo, Chau Ming So, Yixin Lu, and Tamio Hayashi. "A chiral bicyclo[2.2.2]octa-2,5-diene ligand substituted with the ferrocenyl group and its use for rhodium-catalyzed asymmetric 1,4-addition reactions." Organic Chemistry Frontiers 2, no. 2 (2015): 127–32. http://dx.doi.org/10.1039/c4qo00292j.

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18

Gao, Tai-Ping, Dan Liu, Jun-Bing Lin, Xiu-Qin Hu, Zhu-Yin Wang, and Peng-Fei Xu. "Direct construction of chiral quaternary dihydropyranones through highly enantioselective organocatalytic hetero-Diels–Alder reactions of olefinic azlactones." Organic Chemistry Frontiers 3, no. 5 (2016): 598–602. http://dx.doi.org/10.1039/c6qo00018e.

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19

Knölker, Hans-Joachim, Peter Gonser, and Thomas Koegler. "Transition metal-diene complexes in organic synthesis — 29. Separation of planar chiral tricarbonyliron-diene complexes at cyclodextrin bonded chiral stationary phases by HPLC." Tetrahedron Letters 37, no. 14 (1996): 2405–8. http://dx.doi.org/10.1016/0040-4039(96)00326-7.

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20

Miyamura, Hiroyuki, Kohei Nishino, Tomohiro Yasukawa, and Shū Kobayashi. "Rhodium-catalyzed asymmetric 1,4-addition reactions of aryl boronic acids with nitroalkenes: reaction mechanism and development of homogeneous and heterogeneous catalysts." Chemical Science 8, no. 12 (2017): 8362–72. http://dx.doi.org/10.1039/c7sc03025h.

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Asymmetric 1,4-additions of arylboronic acids with nitroalkenes catalyzed by rhodium complexes or heterogeneous Rh–Ag bimetallic nanoparticles with a chiral diene ligand bearing a tertiary butyl amide moiety are developed.

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21

Kanemaguire, LAP, SG Pyne, AFH Siu, BW Skelton, and AH White. "Synthesis, Characterization and Reactions of the Chiral Transfer Agent Dicarbonyl(triphenylphosphine)-[(4r)-phenyl-(1'r)-(1'-phenylethyl)-1-azabuta-1,3-diene]iron(0)." Australian Journal of Chemistry 49, no. 6 (1996): 673. http://dx.doi.org/10.1071/ch9960673.

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The synthesis and room temperature single-crystal X-ray structural characterization of the title compound [( PhCH =CHCH= NCHMePh )Fe(CO)2(PPh3)] are described, the first optically pure 1-azabuta-1,3-diene adduct of iron(0) to be so recorded. Crystals are orthorhombic, P212121, a 20.197(6), b 14.09(1), c 11.094(5) Ǻ, Z 4; conventional R on |F| was 0.061 for 2217 independent 'observed' (I> 3σ(I)) reflections. This compound has been employed to transfer the Fe(CO)2(PPh3) moiety to cyclic 1,3-dienes to give new complexes, including the first example of optically active dicarbonyl ( triphenyl -

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22

Faller, J. W., and Jeremy C. Wilt. "Resolution of BIPHEP on Rh with a chiral diene auxiliary." Journal of Organometallic Chemistry 691, no. 10 (2006): 2207–12. http://dx.doi.org/10.1016/j.jorganchem.2005.09.050.

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23

Nishimura, T., T. Hayashi, Y. Yasuhara, and M. Nagaosa. "New Chiral Diene Ligands for Iridium-Catalyzed [3+2] Annulation." Synfacts 2008, no. 11 (2008): 1190. http://dx.doi.org/10.1055/s-0028-1083447.

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24

Ichikawa, Yoshitaka, Takahiro Nishimura, and Tamio Hayashi. "Rhodium/Chiral Diene-Catalyzed Asymmetric Cyclopolymerization of Achiral 1,8-Diynes." Organometallics 30, no. 8 (2011): 2342–48. http://dx.doi.org/10.1021/om200088q.

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25

Paquin, Jean-François, Christian Defieber, Corey R. J. Stephenson, and Erick M. Carreira. "Asymmetric Synthesis of 3,3-Diarylpropanals with Chiral Diene−Rhodium Catalysts." Journal of the American Chemical Society 127, no. 31 (2005): 10850–51. http://dx.doi.org/10.1021/ja053270w.

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26

Asaoka, Sadayuki, Motohiro Ooi, Peiyun Jiang, Takehiko Wada, and Yoshihisa Inoue. "Enantiodifferentiating photocyclodimerization of cyclohexa-1,3-diene sensitized by chiral arenecarboxylates." Journal of the Chemical Society, Perkin Transactions 2, no. 1 (2000): 77–84. http://dx.doi.org/10.1039/a906826k.

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27

Takechi, Ryosuke, та Takahiro Nishimura. "Rhodium-catalyzed asymmetric addition of arylboronic acids to cyclic N-sulfonyl ketimines towards the synthesis of α,α-diaryl-α-amino acid derivatives". Organic & Biomolecular Chemistry 13, № 17 (2015): 4918–24. http://dx.doi.org/10.1039/c5ob00431d.

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Rhodium/chiral diene complex-catalyzed asymmetric addition of arylboronic acids to cyclic ketimines having an ester group proceeded to give the corresponding α-amino acid derivatives in high yields with high enantioselectivity.

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28

Corell, Mireia, Emile Sheehy, Paul Evans, Nigel Brunton, and Juan Valverde. "Absolute Configuration of Falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol) from Pastinaca Sativa." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800824.

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Falcarinol (9 Z-heptadeca-1,9-diene-4,6-diyn-3-ol; (1) is a polyacetylene commonly found in several plant families. The absolute configuration of naturally occurring 1 is not clear and contradictory results have been reported in the literature. Determination of the absolute configuration of 1 from Pastinaca sativa L. was carried out. Isolation of 95% pure 1 was performed via successive fractionation and preparative-HPLC. A racemic mixture comprised of 3 R-1 and 3 S-1 was synthesized in order to confirm the absolute configuration of the isolated natural product using chiral HPLC. Based on a com

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29

Otomaru, Yusuke, Asato Kina, Ryo Shintani, and Tamio Hayashi. "C2-Symmetric bicyclo[3.3.1]nona-2,6-diene and bicyclo[3.3.2]deca-2,6-diene: new chiral diene ligands based on the 1,5-cyclooctadiene framework." Tetrahedron: Asymmetry 16, no. 9 (2005): 1673–79. http://dx.doi.org/10.1016/j.tetasy.2005.02.022.

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30

Moriyama, Mizuki, Kohei Nakata, Tetsuya Fujiwara, and Yoo Tanabe. "Divergent Asymmetric Total Synthesis of All Four Pestalotin Diastereomers from (R)-Glycidol." Molecules 25, no. 2 (2020): 394. http://dx.doi.org/10.3390/molecules25020394.

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All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asymmetric Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal derived from (R)-glycidol produced a syn-aldol adduct with high diastereoselectivity and enantioselectivity using a Ti(iOPr)4/(S)-BINOL/LiCl catalyst. Diastereoselective Mukaiyama aldol reactions mediated by catalytic achiral Lewis acids directly produced not only a (1′S,6S)-pyrone precursor via the syn-aldol adduct using TiCl4, but also (1′S,6R)

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31

Shaykhutdinova, Polina, and Martin Oestreich. "Further Structural Modification of Sulfur-Stabilized Silicon Cations with Binaphthyl Backbones." Synthesis 51, no. 10 (2019): 2221–29. http://dx.doi.org/10.1055/s-0037-1610697.

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The synthesis and spectroscopic characterization of two novel cationic silicon–sulfur Lewis pairs with a chiral 4,4′-disubstituted binaphthyl silepine backbone are described. Both Lewis acids induce significant enantioselectivity in the model Diels–Alder reaction of cyclohexa-1,3-diene and chalcone but additional substitution of the binaphthyl backbone exerts a minimal effect on enantioinduction compared to previously reported Lewis acids. Another silicon cation with a chiral spirocyclic backbone induces enantioselectivity in the same range but its synthesis is laborious.

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32

Shintani, Ryo, Yoshitaka Ichikawa, Keishi Takatsu, Fu-Xue Chen, and Tamio Hayashi. "Tuning the Chiral Environment ofC2-Symmetric Diene Ligands: Development of 3,7-Disubstituted Bicyclo[3.3.1]nona-2,6-dienes." Journal of Organic Chemistry 74, no. 2 (2009): 869–73. http://dx.doi.org/10.1021/jo802437h.

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33

Li, Jun, Shaoyu An, Chao Yuan, and Pingfan Li. "Enantioselective Protonation of Silyl Enol Ethers Catalyzed by a Chiral Pentacarboxycyclopentadiene-Based Brønsted Acid." Synlett 30, no. 11 (2019): 1317–20. http://dx.doi.org/10.1055/s-0037-1611849.

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The enantioselective protonation of silyl enol ethers was realized in the presence of a pentacarboxycyclopenta-1,3-diene-based chiral Brønsted acid catalyst with water as an achiral proton source to give the corresponding α-aryl ketones in good yields and up to 75% ee.

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34

Nishimura, Takahiro, Akram Ashouri, Yusuke Ebe, Yuko Maeda, and Tamio Hayashi. "Rhodium/chiral diene-catalyzed asymmetric methylation of N-sulfonylarylimines with trimethylboroxine." Tetrahedron: Asymmetry 23, no. 9 (2012): 655–58. http://dx.doi.org/10.1016/j.tetasy.2012.04.021.

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35

Carbery, David, Nathan Fairhurst, and Rachel Munday. "Simple Oxazolidine Chiral Diene Ligands for Enantioselective Rh-Catalyzed Conjugate Additions." Synlett 24, no. 04 (2013): 496–98. http://dx.doi.org/10.1055/s-0032-1318135.

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36

Hayashi, T., R. Shintani та K. Okamoto. "Rh/Chiral Diene-Catalyzed Enantioselective 1,4-Addition to β-Silyl Enones". Synfacts 2006, № 01 (2005): 0064. http://dx.doi.org/10.1055/s-2005-921731.

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37

Pertici, Paolo, Giovanni Vitulli, Sergio Bertozzi та Raffaello Lazzaroni. "Synthesis of new chiral (η6-arene)(η4-diene)ruthenium(O) complexes". Inorganica Chimica Acta 149, № 2 (1988): 235–39. http://dx.doi.org/10.1016/s0020-1693(00)86074-0.

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38

Shibata, T., and Y.-k. Tahara. "Chiral Quaternary Carbon Stereocenters via Diene-yne [2+2+2] Cycloaddition." Synfacts 2007, no. 1 (2007): 0069. http://dx.doi.org/10.1055/s-2006-955725.

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39

Dong, Han-Qing, Ming-Hua Xu, Chen-Guo Feng, Xing-Wen Sun, and Guo-Qiang Lin. "ChemInform Abstract: Recent Applications of Chiral N-tert-Butanesulfinyl Imines, Chiral Diene Ligands and Chiral Sulfur-Olefin Ligands in Asymmetric Synthesis." ChemInform 46, no. 17 (2015): no. http://dx.doi.org/10.1002/chin.201517313.

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40

Takemoto, Yoshiji, Naoki Yoshikawa, Yasutaka Baba, et al. "Utility of a Diene−Tricarbonyliron Complex as a Mobile Chiral Auxiliary: Regio- and Stereocontrolled Functionalization of Acyclic Diene Ligands." Journal of the American Chemical Society 121, no. 39 (1999): 9143–54. http://dx.doi.org/10.1021/ja991889q.

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41

Pearson, Anthony J., Sheri L. Blystone, and Brian A. Roden. "Chiral recognition during the reaction between diene-Mo(CO)2Cp cations and enolate nucleophiles bearing chiral auxiliaries." Tetrahedron Letters 28, no. 22 (1987): 2459–62. http://dx.doi.org/10.1016/s0040-4039(00)95440-6.

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42

Takemoto, Yoshiji, Toshiro Ibuka, Yoshiji Takemoto, et al. "Utility of a diene–tricarbonyliron complex as mobile chiral auxiliary: iterative use for constructing contiguous chiral centers." Chemical Communications, no. 17 (1998): 1911–12. http://dx.doi.org/10.1039/a805171b.

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43

Hatano, Miyuki, та Takahiro Nishimura. "Hydroxoiridium/Chiral Diene Complexes as Effective Catalysts for Asymmetric Annulation of α-Oxo- and Iminocarboxamides with 1,3-Dienes". Angewandte Chemie 127, № 37 (2015): 11099–102. http://dx.doi.org/10.1002/ange.201505382.

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44

Hatano, Miyuki, та Takahiro Nishimura. "Hydroxoiridium/Chiral Diene Complexes as Effective Catalysts for Asymmetric Annulation of α-Oxo- and Iminocarboxamides with 1,3-Dienes". Angewandte Chemie International Edition 54, № 37 (2015): 10949–52. http://dx.doi.org/10.1002/anie.201505382.

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45

Sakakura, Akira, Yudai Fujii, Ryota Nakao, et al. "Enantioselective Diels–Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts." Synlett 31, no. 20 (2020): 2013–17. http://dx.doi.org/10.1055/s-0040-1707302.

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AbstractAn enantioselective Diels–Alder reaction of 3-nitrocoumarins has been developed. A tryptophan-derived C 1-symmetric organoammonium thiourea catalyst promoted the reaction of 3-nitrocoumarins with Danishefsky’s diene to give the corresponding adducts with good enantioselectivity (up to 94% ee). One of the resulting adducts was converted into a chiral carbocyclic quaternary β-amino alcohol.

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46

Cabrera, Silvia, Olga García Mancheño, Ramón Gómez Arrayás, Inés Alonso, Pablo Mauleón, and Juan C. Carretero. "Sulfenylphosphinoferrocenes: Novel planar chiral ligands in enantioselective catalysis." Pure and Applied Chemistry 78, no. 2 (2006): 257–65. http://dx.doi.org/10.1351/pac200678020257.

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Structurally well-defined transition-metal complexes of 1-phosphino-2-sulfenylferrocene (Fesulphos ligands) act as highly efficient catalysts in a variety of mechanistically different transformations. Excellent enantioselectivities were achieved in Pd-catalyzed allylic substitutions, desymmetrization of meso-heterobicyclic alkenes by Pd-catalyzed addition of dialkylzinc reagents, Pd-catalyzed Diels-Alder reaction of cyclopentadiene with N-acryloyl oxazolidinones, and in Cu-catalyzed formal aza-Diels-Alder reaction of Danishefsky diene to N-sulfonyl aldimines.

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47

Hirano, Masafumi, Nobuyuki Komine, Eri Arata, et al. "Recent advances of achiral and chiral diene ligands in transition-metal catalyses." Tetrahedron Letters 60, no. 37 (2019): 150924. http://dx.doi.org/10.1016/j.tetlet.2019.07.015.

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48

Lanari, D., A. Marrocchi, L. Minuti, C. Rosini, S. Superchi, and A. Taticchi. "Synthesis and absolute configuration of a new chiral [2.2]paracyclophane-based diene." Tetrahedron: Asymmetry 13, no. 12 (2002): 1257–63. http://dx.doi.org/10.1016/s0957-4166(02)00330-0.

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49

Takechi, Ryosuke, and Takahiro Nishimura. "Enantioselective 1,4-addition of cyclopropylboronic acid catalyzed by rhodium/chiral diene complexes." Chemical Communications 51, no. 40 (2015): 8528–31. http://dx.doi.org/10.1039/c5cc02140e.

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50

Pattenden, Gerald, Douglas J. Critcher, and Modesto Remuiñán. "Total synthesis of ()-pateamine A, a novel immunosuppressive agent from Mycale sp." Canadian Journal of Chemistry 82, no. 2 (2004): 353–65. http://dx.doi.org/10.1139/v03-199.

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A convergent synthesis of the unique thiazole-containing polyene bis-lactone pateamine A (1) isolated from the marine sponge Mycale sp is described. The synthesis features the ubiquitous Stille sp2sp2 coupling reaction to elaborate the E,Z-diene macrolide core 23 and the all-E polyenamine side chain in the natural product. It also highlights the scope for enantiopure sulfinimine intermediates in the synthesis of chiral β-amino ester moieties in complex structures.Key words: pateamine A, immunosuppressive agent from marine sponge Mycale sp, total synthesis, novel 19-membered bis-lactone, thiaz

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