Synthesis of homochiral piperidine derivatives from S-glutamic acid. Stereoselective 1,4-addition of organocuprates to a Delta(3)-piperidine-2-one. A paroxetine analogue.

被引：34

作者：

Herdeis, C ^{[1
]}

Kaschinski, C ^{[1
]}

Karla, R ^{[1
]}

Lotter, H ^{[1
]}

机构：

[1] UNIV MUNICH,INST PHARMAZEUT BIOL,D-80333 MUNICH,GERMANY

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 03期

关键词：

D O I：

10.1016/0957-4166(96)00085-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantiomerically pure S-5-hydroxy-2-piperidinone 4, readily available from S-glutamic acid, serves as a key intermediate for the synthesis of 3,4-trans substituted piperidine derivatives. The substituents in the 4-position are introduced via 1,4 conjugate organocuprate addition to 7 with excellent trans selectivity. This reaction is employed for the synthesis of a paroxetine analogue 21g. All attempts to transform 16 to (+)-meroquinene 17 failed. (C) 1996 Elsevier Science Ltd

引用

页码：867 / 884

页数：18

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