Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements:: chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3-methylproline and (-)-kainic acid

被引：34

作者：

Anderson, JC ^{[1
]}

O'Loughlina, JMA

Tornos, JA

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] AstraZeneca, Proc Res & Dev, Loughborough LE11 5RH, Leics, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 15期

关键词：

D O I：

10.1039/b506198a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A survey of 16 different chiral auxiliaries and a variety of strategies found that an (-)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of aza-[2,3]-Wittig sigmatropic rearrangements with diastereoselectivities of ca. 3 : 1 with respect to the auxiliary. In two specific examples, ca. 50% yields of enantiomerically pure products were obtained after chromatographic purification. These were synthetically manipulated with no erosion of stereochemistry into intermediates that completed formal asymmetric syntheses of (+)- HyMePro and (-)- kainic acid.

引用

页码：2741 / 2749

页数：9

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