Convenient multigram synthesis of (R)-homopipecolic acid methyl ester

被引:6
|
作者
Breuning, M [1 ]
Steiner, M [1 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
来源
SYNTHESIS-STUTTGART | 2006年 / 08期
关键词
piperidines; stereoselective synthesis; beta-amino ester; Michael additions; fractional crystallization;
D O I
10.1055/s-2006-926419
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(R)-Homopipecolic acid methyl ester has been prepared on a multigrant scale from 3,4-dihydro-2H-pyran in five steps and 36% overall yield. The stereochemistry was introduced via an asymmetric Michael addition and a fractional crystallization.
引用
收藏
页码:1386 / 1389
页数:4
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