delta-Amino beta-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis. Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A.
[formula: see text] delta-Amino beta-keto esters 3 and 11 are designed polyfunctionalized chiral building blocks for alkaloid synthesis and are prepared in one step from the corresponding sulfinimine (N-sulfinyl imine). Concise highly enantioselective four-step syntheses of 2-phenylpiperidine (7) and SS20846A (14) from 3 and 11, respectively, are described.
Davis
F A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@astro.ocis.temple.edu
Chao
B
B
Fang
T
T
Szewczyk
J M
JM
D000470:Alkaloids / Q000737:chemistry*; D004952:Esters; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry
C408865:2-phenylpiperidine; D000470:Alkaloids; D004952:Esters; D010880:Piperidines; C408864:SS 20846A