Enantioselective synthesis of cis- and trans-3,5-disubstituted piperidines.: Synthesis of 20S- and 20R-dihydrocleavamine

被引：27

作者：

Amat, M ^{[1
]}

Escolano, C ^{[1
]}

Lozano, O ^{[1
]}

Llor, N ^{[1
]}

Bosch, J ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 17期

关键词：

D O I：

10.1021/ol035199+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective alkylation at the carbonyl alpha-position of chiral nonracemic lactams 2 and 3, the former prepared by cyclocondensation of (R)-phenylglycinol with a racemic gamma-substituted delta-oxoester in a process that involves a dynamic kinetic resolution and the latter by a subsequent equilibration, provides access to enantiopure cis- and trans-3,5-disubstituted piperidines. The usefulness of the approach is illustrated with the synthesis of the alkaloids 20S- and 20R-15,20-dihydrocleavamine.

引用

页码：3139 / 3142

页数：4

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