Studies on the oxidation of 2,2,4-trisubstituted 3-pyrrolines

被引：12

作者：

Green, MP

Prodger, JC

Hayes, CJ

机构：

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

[2] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(02)00285-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As part of our studies directed towards a total synthesis of lactacystin, we have developed a reliable and environmentally acceptable method to oxidise 2,2,4-trisubstituted 3-pyrrolines to the corresponding 3-pyrrolin-2-ones. Several protocols were examined and the two-step (i) TPAP/NMO; (ii) sodium hypochlorite allylic oxidation was found to be the most satisfactory. Catalytic oxidation of the 3-pyrroline afforded the corresponding cyclic imine in high yield, and subsequent oxidation with NaOCl afforded the N-chloro-3-pyrrolin-2-one. The N-chloro-substituent was removed by a simple acid treatment. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：2649 / 2652

页数：4

共 21 条

[1] Stereoselective total synthesis of (+)-lactacystin from D-glucose [J].