Control of diastereoselectivity by solvent effects in the addition of Grignard reagents to enantiopure t-butylsulfinimine:: Syntheses of the Stereoisomers of the hydroxyl derivatives of sibutramine

被引：31

作者：

Lu, BZ ^{[1
]}

Senanayake, C ^{[1
]}

Li, NS ^{[1
]}

Han, ZX ^{[1
]}

Bakale, RP ^{[1
]}

Wald, SA ^{[1
]}

机构：

[1] Sepracor Inc, Chem Proc Res & Dev, Marlborough, MA 01752 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 13期

关键词：

D O I：

10.1021/ol0507017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method has been developed to prepare all four isomers of the hydroxyl derivatives of sibutramine by addition of Grignard reagents (R)- or (S)-5 to a single enantiomer of sulfinyl imine (R)-1 simply by tuning the reaction solvent. The phenomenon of the reversed diastereoselectivity in CH2Cl2 and THF implied that the reaction may proceed through a chelated cyclic transition state in CH2Cl2 and nonchelated acyclic transition state in THF.

引用

页码：2599 / 2602

页数：4

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