Asymmetric synthesis of (+) and (-) trans-2,6-dimethylpiperidines

被引：27

作者：

Freville, S ^{[1
]}

Bonin, M ^{[1
]}

Celerier, JP ^{[1
]}

Husson, HP ^{[1
]}

Lhommet, G ^{[1
]}

Quirion, JC ^{[1
]}

Thuy, VM ^{[1
]}

机构：

[1] UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CNRS,CHIM THERAPEUT LAB,F-75270 PARIS 06,FRANCE

来源：

TETRAHEDRON | 1997年 / 53卷 / 25期

关键词：

D O I：

10.1016/S0040-4020(97)00525-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+) and (-) trans-2,6-dimethylpiperidines 9 have been prepared from diastereomeric lactams 6 and 11, both available from (R)-(-)-phenylglycinol 4. Diastereoselective C-2 alkylation afforded oxazolidines 7 and 12. Reduction of 7 with LiAlH4 or NaBH4 led to trans-2,6-8 with total retention of configuration; When 12 was reduced with NaBH4, irans derivative 13a was isolated as the major isomer. A mechanism is proposed to explain the different results. (C) 1997 Elsevier Science Ltd.

引用

页码：8447 / 8456

页数：10

共 14 条

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