delta-amino beta-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis. Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A

Authors
Davis, FA Chao, B Fang, TN Szewczyk, JM
Citation
Fa. Davis et al., delta-amino beta-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis. Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A, ORG LETT, 2(8), 2000, pp. 1041-1043
Citations number
36
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
8
Year of publication
2000
Pages
1041 - 1043
Database
ISI
SICI code
1523-7060(20000420)2:8<1041:DBEADP>2.0.ZU;2-E
Abstract
delta-Amino beta-keto esters 3 and 11 are designed polyfunctionalized chira l building blocks for alkaloid synthesis and are prepared in one step from the corresponding sulfinimine (N-sulfinyl imine). Concise highly enantiosel ective four step syntheses of 2-phenylpiperidine (7) and SS20846A (14) from 3 and 11, respectively, are described.