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Direct asymmetric synthesis of beta-amino ketones from sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B.
Org Lett. 2003 Dec 25; 5(26):5011-4.OL

Abstract

N-Sulfinyl beta-amino ketones, prepared directly from the potassium enolates of methyl ketones and enantiopure sulfinimines, are transformed in one pot to protected amino ketones, which are valuable chiral building blocks for the assembly of piperidines. The utility of this methodology is illustrated in a concise asymmetric synthesis of (-)-indolizidine 209B. [reaction: see text]

Authors+Show Affiliations

Davis FA
Department of Chemistry, Temple University, Philadelphia, PA 19122, USA. fdavis@temple.edu
Yang B
No affiliation info available

MeSH

AlkaloidsIminesIndolizinesKetonesPiperidinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

14682752

Citation

Davis, Franklin A., and Bin Yang. "Direct Asymmetric Synthesis of Beta-amino Ketones From Sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B." Organic Letters, vol. 5, no. 26, 2003, pp. 5011-4.
Davis FA, Yang B. Direct asymmetric synthesis of beta-amino ketones from sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B. Org Lett. 2003;5(26):5011-4.
Davis, F. A., & Yang, B. (2003). Direct asymmetric synthesis of beta-amino ketones from sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B. Organic Letters, 5(26), 5011-4.
Davis FA, Yang B. Direct Asymmetric Synthesis of Beta-amino Ketones From Sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B. Org Lett. 2003 Dec 25;5(26):5011-4. PubMed PMID: 14682752.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric synthesis of beta-amino ketones from sulfinimines (N-sulfinylimines). Synthesis of (-)-indolizidine 209B. AU - Davis,Franklin A, AU - Yang,Bin, PY - 2003/12/20/pubmed PY - 2004/10/27/medline PY - 2003/12/20/entrez SP - 5011 EP - 4 JF - Organic letters JO - Org Lett VL - 5 IS - 26 N2 - N-Sulfinyl beta-amino ketones, prepared directly from the potassium enolates of methyl ketones and enantiopure sulfinimines, are transformed in one pot to protected amino ketones, which are valuable chiral building blocks for the assembly of piperidines. The utility of this methodology is illustrated in a concise asymmetric synthesis of (-)-indolizidine 209B. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/14682752/Direct_asymmetric_synthesis_of_beta_amino_ketones_from_sulfinimines__N_sulfinylimines___Synthesis_of_____indolizidine_209B_ DB - PRIME DP - Unbound Medicine ER -