Stereoselective synthesis of 5-(1-hydroxyalkyl)-pyrrolidinones utilizing oxidation of 5-alkylidene-2-pyrrolidinones to acyliminium ion precursors

被引：45

作者：

Koseki, Y ^{[1
]}

Kusano, S ^{[1
]}

Ichi, D ^{[1
]}

Yoshida, K ^{[1
]}

Nagasaka, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 45期

关键词：

acyliminium ion; cyclization; oxidation; pyrrolidinone;

D O I：

10.1016/S0040-4020(00)00841-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method was devised for the LiN(TMS)(2)/AgOTf (=2:1)-catalyzed intramolecular (5-exo-dig) cyclization of beta -alkynylamides 1 possessing alkyl, aryl or no functional groups at the terminal alkynes, to 5-alkylidene-2-pyrrolidinones 2. These 5-alkylidene-2-pyrrolidinones were oxidized to the diol-type alkoxylactams 3 by dimethyldioxirane (DMD) or mCPBA in MeOH. These alkoxylactams are useful as tertiary N-acyliminium ion precursors for the synthesis of threo-5-(1-hydroxyalkyl)-2-pyrrolidinone derivatives 5. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8855 / 8865

页数：11

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