Alkylation of phenylglycinol-derived oxazolopiperidone lactams.: Enantioselective synthesis of β-substituted piperidines

被引：34

作者：

Amat, M ^{[1
]}

Escolano, C

Lozano, O

Gomez-Esque, A

Griera, R

Molins, E

Bosch, J

机构：

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

[2] CSIC, Inst Ciencia Mat, Cerdanyola Del Valles 08193, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 10期

关键词：

D O I：

10.1021/jo060157v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemical outcome of the alkylation of a variety of phenylglycinol-derived oxazolopiperidone lactams is studied. The influence of the configuration of the C-8a stereocenter and the effect of the substituents at the C-8 and C-8a positions on the stereoselectivity of the reaction are discussed. The synthetic utility of these alkylation reactions is illustrated with the synthesis of cis and trans 3,5-disubstituted, 2,5-disubstituted, and 2,3,5-trisubstituted enantiopure piperidines, and the indole alkaloids 20R- and 20S-dihydrocleavamine.

引用

页码：3804 / 3815

页数：12

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