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Relevant bibliographies by topics / Diastereoselective reductive amination

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Academic literature on the topic 'Diastereoselective reductive amination'

Author: Grafiati

Published: 9 March 2023

Last updated: 10 March 2023

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Journal articles on the topic "Diastereoselective reductive amination"

1

Menche, D., F. Arikan, J. Li, and S. Rudolph. "Diastereoselective Reductive Amination of β-Hydroxyketones." Synfacts 2007, no. 4 (April 2007): 0424. http://dx.doi.org/10.1055/s-2007-968324.

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2

Sviridova, L. A., G. A. Golubeva, A. N. Tavtorkin, Yu V. Nelyubina, and K. A. Kochetkov. "Diastereoselective reductive amination of pyrazolidinyl alkyl ketones." Chemistry of Heterocyclic Compounds 44, no. 5 (May 2008): 542–48. http://dx.doi.org/10.1007/s10593-008-0073-x.

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3

Salmi, Chanaz, Yves Letourneux, and Jean Brunel. "Efficient Diastereoselective Titanium(IV) Reductive Amination of Ketones." Letters in Organic Chemistry 3, no. 5 (May 1, 2006): 384–89. http://dx.doi.org/10.2174/157017806776611971.

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4

Hughes, Greg, Paul N Devine, John R Naber, Paul D O'Shea, Bruce S Foster, Daniel J McKay, and R. P. Volante. "Diastereoselective Reductive Amination of Aryl Trifluoromethyl Ketones and α-Amino Esters." Angewandte Chemie 119, no. 11 (March 5, 2007): 1871–74. http://dx.doi.org/10.1002/ange.200603745.

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5

Hughes, Greg, Paul N Devine, John R Naber, Paul D O'Shea, Bruce S Foster, Daniel J McKay, and R. P. Volante. "Diastereoselective Reductive Amination of Aryl Trifluoromethyl Ketones and α-Amino Esters." Angewandte Chemie International Edition 46, no. 11 (March 5, 2007): 1839–42. http://dx.doi.org/10.1002/anie.200603745.

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6

CONCIALINI, V., S. ROFFIA, and D. SAVOIA. "ChemInform Abstract: Diastereoselective Electrochemical Reductive Amination of 2,5- Hexanedione and 2,6-Heptanedione." ChemInform 26, no. 33 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199533137.

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7

Ryu, Jae-Sang, Yunjeong Park, and Jae Lee. "Synthesis of a Cyclic Analogue of Tuv N-Methyl Tubulysin." Synlett 26, no. 08 (March 9, 2015): 1063–68. http://dx.doi.org/10.1055/s-0034-1379900.

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Tubulysins are the most potent antimitotic agents known so far. We are interested in the conformational effect of tubulysin and herein we report the design and synthesis of a conformationally rigid cyclic analogue of Tuv N-methyl tubulysin. A conformationally rigid tetrahydropyran moiety was incorporated into the Tuv fragment via enantioselective hetero Diels–Alder reaction to prevent the rotation of the Tuv chain. The following diastereoselective reductive amination yielded the (4-methylamino)tetrahydropyranyl Tuv fragment, which was coupled to d-Mep-l-Ile dipeptide fragment and Tup fragment sequentially.

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8

Bunce, Richard A., Derrick M. Herron, Lara B. Johnson, and Sharadsrikar V. Kotturi. "Diastereoselective Synthesis of Substituted Tetrahydroquinoline-4-carboxylic Esters by a Tandem Reduction−Reductive Amination Reaction." Journal of Organic Chemistry 66, no. 8 (April 2001): 2822–27. http://dx.doi.org/10.1021/jo001761n.

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9

Bunce, Richard A., Derrick M. Herron, Jason R. Lewis, Sharadsrikar V. Kotturi, and Elizabeth M. Holt. "Diastereoselective synthesis of linear-fused tricyclic nitrogen heterocycles by a tandem reduction-reductive amination reaction." Journal of Heterocyclic Chemistry 40, no. 1 (January 2003): 101–6. http://dx.doi.org/10.1002/jhet.5570400113.

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10

Bunce, Richard A., Derrick M. Herron, Lara B. Johnson, and Sharadsrikar V. Kotturi. "ChemInform Abstract: Diastereoselective Synthesis of Substituted Tetrahydroquinoline-4-carboxylic Esters by a Tandem Reduction-Reductive Amination Reaction." ChemInform 32, no. 36 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200136139.

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Dissertations / Theses on the topic "Diastereoselective reductive amination"

1

JONAS, Hendrik. "Stereoselective Synthesis and Pharmacological Evaluation of 2,4-Bridged Piperidine Derivatives Designed to Activate the κ-Opioid Receptor." Doctoral thesis, Università degli Studi di Palermo, 2021. http://hdl.handle.net/10447/518592.

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Book chapters on the topic "Diastereoselective reductive amination"

1

Taber, Douglass F. "Synthesis of C-N Natural Products: (-)-α-Kainic Acid (Helmchen), (+)-Tylophorine (Opatz), (-)-Lycoperine A (Rychnovsky), Fluvirucidine A2 (Suh), Complanidine A (Sarpong)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0058.

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Günter Helmchen of the Ruprecht-Karls-Universität Heidelberg set (Organic Lett. 2010, 12, 1108) the absolute configuration of 3 by Ir*-mediated coupling of 1 with 2. Diastereoselective Pauson-Khand cyclization then led to (-)-α-kainic acid 5. Till Opatz, now at the Johannes Gutenberg-Universität Mainz, showed (Organic Lett. 2010, 12, 2140) that the product from the Dibal reduction of 6 could be condensed with the amine 7 without epimerization. Kim cyclization then directly delivered the pentacyclic alkaloid (+)-tylophorine 9. The interesting dimeric alkaloid lycoperine A 13 was recently isolated from the Japanese club moss Lycopodium hamiltonii. Scott D. Rychnovsky of the University of California, Irvine, prepared (Organic Lett. 2010, 12, 72) 12 by double alkylation of the bis-nitrile 11 with the enantiomerically pure allylic bromide 10. Although the projected reductive decyanation of 12 failed, hydrolysis followed by diastereoselective reductive amination successfully gave 13. Retrosynthetic analysis of fluvirucinine A2 16 could lead to an acyclic amino acid, which could be cyclized to the macrolactam. Young-Ger Suh of Seoul National University took (Organic Lett. 2010, 12, 2040) a different approach, building up the 14-membered ring system by two four-carbon ring expansions, beginning with an enantiomerically pure piperidine precursor. The second of these enolate-based aza-Claisen ring expansions is illustrated in the conversion of 14 to 15. Richmond Sarpong of the University of California, Berkeley, faced (J. Am. Chem. Soc. 2010, 132, 5926) a different sort of challenge in the synthesis of the dimeric Lycopodium alkaloid complanadine A 19. Even with established access to monomers such as 17 and its precursors, it was not clear how the 5-position of the pyridine ring could be selectively activated for bond formation. The solution to this dilemma was found in the work of Hartwig. Following that precedent, Ir-catalyzed activation of 17 converted it cleanly into the borinate 18, which could then be coupled with a pyridone triflate to complete the synthesis of 19.

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2

Taber, Douglass. "The Takayama Synthesis of (-)-Cernuine." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0094.

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(-)-Cernuine 3 falls in the subset of the Lycopodium alkaloids that feature a bicyclic aminal core. There had not been a total synthesis of this class of alkaloids until the recent (Organic Lett. 2008, 10, 1987) work of Hiromitsu Takayama of Chiba University. The key step in this synthesis was a diastereoselective intramolecular reductive amination, converting 1 to 2. As is apparent from the 3-D projection, (-)-cernuine 3 has a tricyclic trans-anti-trans aminal core, with an appended six-membered ring, both branches of which are axial on the core. While the branch that is part of the aminal could be expected to equilibrate, the other branch had to be deliberately installed. The synthesis began with (+)-citronellal 4, each enantiomer of which is commercially available in bulk. After protection and ozonolysis, the first singly-aminated stereogenic center was installed by enantioselective, and therefore diastereoselective, addition of 5 to the azodicarboxylate 6, mediated by the organocatalyst 7. Reductive cleavage of the N-N bond followed by acetal methanolysis converted 8 to 9. Ionization followed by allyl silane addition then delivered 11, having the requisite axial alkyl branch. The next two tasks were the assembly of the second of the four rings of 3, and the construction of the second single-aminated stereogenic center. The ring was assembled by deprotection of 11 followed by acylation with acryloyl chloride, to give 12. Grubbs cyclization followed by hydrogenation then led to 13. Homologation of 13 to the aldehyde 14 set the stage for condensation with the camphor-derived tertiary amine 15, following the protocol developed by Kobayashi. Sequential imine formation, aza-Cope rearrangement, and hydrolysis led to 1 in 94% de. One could envision reduction of the lactam carbonyl of 1 to an aldehyde equivalent, that would then, under acidic conditions, condense to form the desired aminal 2. This approach was, however, not successful. As an alternative, conditions were developed to convert 1 to the amidine 16. Reduction then proceeded with the expected high diastereocontrol, to give the cis 1,3-fused aminal 2. This was not isolated, but was directly acylated with acryloyl chloride, to 17.

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