Tags

Type your tag names separated by a space and hit enter

Asymmetric synthesis and applications of beta-amino Weinreb amides: asymmetric synthesis of (S)-coniine.
Org Biomol Chem. 2004 May 07; 2(9):1387-94.OB

Abstract

Conjugate addition of lithium (S)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha, beta-unsaturated Weinreb amides proceeds with high levels of diastereoselectivity (>95% de). The beta-amino Weinreb amide products may be transformed into beta-amino ketones via reactions with Grignard reagents, while treatment with DIBAL-H furnishes beta-amino aldehydes. Trapping of the aldehyde via Wadsworth-Emmons reaction and subsequent manipulation offers an efficient route to homochiral delta-amino acid derivatives and 2-substituted piperidines. The application of this methodology for the synthesis of (S)-coniine is demonstrated.

Authors+Show Affiliations

Burke AJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK OX1 3TA.
Davies SG
No affiliation info available
Garner AC
No affiliation info available
McCarthy TD
No affiliation info available
Roberts PM
No affiliation info available
Smith AD
No affiliation info available
Rodriguez-Solla H
No affiliation info available
Vickers RJ
No affiliation info available

MeSH

AldehydesAlkaloidsAmidesKetonesLithium CompoundsMolecular StructurePiperidines

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15105931

Citation

Burke, Anthony J., et al. "Asymmetric Synthesis and Applications of Beta-amino Weinreb Amides: Asymmetric Synthesis of (S)-coniine." Organic & Biomolecular Chemistry, vol. 2, no. 9, 2004, pp. 1387-94.
Burke AJ, Davies SG, Garner AC, et al. Asymmetric synthesis and applications of beta-amino Weinreb amides: asymmetric synthesis of (S)-coniine. Org Biomol Chem. 2004;2(9):1387-94.
Burke, A. J., Davies, S. G., Garner, A. C., McCarthy, T. D., Roberts, P. M., Smith, A. D., Rodriguez-Solla, H., & Vickers, R. J. (2004). Asymmetric synthesis and applications of beta-amino Weinreb amides: asymmetric synthesis of (S)-coniine. Organic & Biomolecular Chemistry, 2(9), 1387-94.
Burke AJ, et al. Asymmetric Synthesis and Applications of Beta-amino Weinreb Amides: Asymmetric Synthesis of (S)-coniine. Org Biomol Chem. 2004 May 7;2(9):1387-94. PubMed PMID: 15105931.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis and applications of beta-amino Weinreb amides: asymmetric synthesis of (S)-coniine. AU - Burke,Anthony J, AU - Davies,Stephen G, AU - Garner,A Christopher, AU - McCarthy,Tom D, AU - Roberts,Paul M, AU - Smith,Andrew D, AU - Rodriguez-Solla,Humberto, AU - Vickers,Richard J, Y1 - 2004/04/05/ PY - 2004/4/24/pubmed PY - 2005/4/30/medline PY - 2004/4/24/entrez SP - 1387 EP - 94 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 2 IS - 9 N2 - Conjugate addition of lithium (S)-N-benzyl-N-alpha-methylbenzylamide to a range of alpha, beta-unsaturated Weinreb amides proceeds with high levels of diastereoselectivity (>95% de). The beta-amino Weinreb amide products may be transformed into beta-amino ketones via reactions with Grignard reagents, while treatment with DIBAL-H furnishes beta-amino aldehydes. Trapping of the aldehyde via Wadsworth-Emmons reaction and subsequent manipulation offers an efficient route to homochiral delta-amino acid derivatives and 2-substituted piperidines. The application of this methodology for the synthesis of (S)-coniine is demonstrated. SN - 1477-0520 UR - https://www.unboundmedicine.com/medline/citation/15105931/Asymmetric_synthesis_and_applications_of_beta_amino_Weinreb_amides:_asymmetric_synthesis_of__S__coniine_ DB - PRIME DP - Unbound Medicine ER -