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Asymmetric synthesis of anti-α-substituted β-amino ketones from sulfinimines.
J Org Chem. 2011 May 06; 76(9):3329-37.JO

Abstract

Previously unknown, enantiopure, β-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-α-substituted β-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-α-substituted isomers which did. The anti-α-substituted β-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-α-substituted β-amino esters because α-alkylation of N-sulfinyl β-amino Weinreb amide enolates resulted in poor diastereoselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Davis FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Xu P
No affiliation info available

MeSH

IminesKetonesStereoisomerismSubstrate Specificity

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

21417438

Citation

Davis, Franklin A., and Peng Xu. "Asymmetric Synthesis of Anti-α-substituted Β-amino Ketones From Sulfinimines." The Journal of Organic Chemistry, vol. 76, no. 9, 2011, pp. 3329-37.
Davis FA, Xu P. Asymmetric synthesis of anti-α-substituted β-amino ketones from sulfinimines. J Org Chem. 2011;76(9):3329-37.
Davis, F. A., & Xu, P. (2011). Asymmetric synthesis of anti-α-substituted β-amino ketones from sulfinimines. The Journal of Organic Chemistry, 76(9), 3329-37. https://doi.org/10.1021/jo2002352
Davis FA, Xu P. Asymmetric Synthesis of Anti-α-substituted Β-amino Ketones From Sulfinimines. J Org Chem. 2011 May 6;76(9):3329-37. PubMed PMID: 21417438.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of anti-α-substituted β-amino ketones from sulfinimines. AU - Davis,Franklin A, AU - Xu,Peng, Y1 - 2011/04/01/ PY - 2011/3/23/entrez PY - 2011/3/23/pubmed PY - 2011/8/19/medline SP - 3329 EP - 37 JF - The Journal of organic chemistry JO - J Org Chem VL - 76 IS - 9 N2 - Previously unknown, enantiopure, β-amino ketones were prepared in modest yield by addition of lithium reagents to N-sulfinyl anti-α-substituted β-amino Weinreb amides. Grignard reagents failed to add to these Weinreb amides in contrast to the syn-α-substituted isomers which did. The anti-α-substituted β-amino Weinreb amides were prepared by addition of LiN(OMe)Me to the corresponding N-sulfinyl anti-α-substituted β-amino esters because α-alkylation of N-sulfinyl β-amino Weinreb amide enolates resulted in poor diastereoselectivities. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/21417438/Asymmetric_synthesis_of_anti_α_substituted_β_amino_ketones_from_sulfinimines_ L2 - https://doi.org/10.1021/jo2002352 DB - PRIME DP - Unbound Medicine ER -