N-Sulfinyl Amines as a Nitrogen Source in the Asymmetric Intramolecular Aza-Michael Reaction: Total Synthesis of (-)-Pinidinol

被引：75

作者：

Fustero, Santos ^{[1
,2
]}

Monteagudo, Silvia ^{[1
]}

Sanchez-Rosello, Maria ^{[2
]}

Flores, Sonia ^{[1
]}

Barrio, Pablo ^{[1
]}

del Pozo, Carlos ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

[2] Ctr Invest Principe Felipe, Lab Mol Organ, Valencia 46012, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 32期

关键词：

aza-Michael reaction; cross metathesis; sullinylamines; piperidines; pyrrolidines; TERT-BUTANESULFINYL IMINES; CONJUGATE ADDITION; CHIRAL AUXILIARIES; CONCISE SYNTHESIS; PIPERIDINES; ALKALOIDS; ROUTE; ACID; ORGANOCATALYSIS; PHOSPHONATES;

D O I：

10.1002/chem.201000615

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Sulfinyl amines have been successfully employed as nitrogen nucleophiles for the asymmetric intramolecular aza-Michael reaction. The synthetic strategy involves a cross-metathesis reaction followed by the Michael-type cyclization. either in a base-catalyzed two-step procedure or in a tandem fashion The (developed methodology allows access to chiral substituted pyrrolidines and piperidines bearing one or two stereocenters and it has been applied to the synthesis of the piperidine alkaloid (-)-pinidinol

引用

页码：9835 / 9845

页数：11

共 54 条

[1] Asymmetric routes to substituted piperidines [J].