Asymmetric synthesis of azetidin-2-ones by [2+2] cycloaddition using chiral imines derived from D-(+)-glucose

被引：33

作者：

Arun, M

Joshi, SN

Puranik, VG

Bhawal, BM

Deshmukh, ARAS ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Synth, Pune 411008, Maharashtra, India

[2] Natl Chem Lab, Div Phys Chem, Pune 411008, Maharashtra, India

[3] Emcure Pharmaceut Ltd, Pune 411026, Maharashtra, India

来源：

TETRAHEDRON | 2003年 / 59卷 / 13期

关键词：

asymmetric synthesis; ketenes; imines; Staudinger reaction;

D O I：

10.1016/S0040-4020(03)00239-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric synthesis of beta-lactams by the [2+2] cycloaddition of ketenes with chiral imines derived from D-(+)-glucose was carried out; predominantly cis-beta-lactams were formed with very high diastereoselectivity. The stereochemistry at C-3 and C-4 was established as 3S and 4R from the known absolute configuration of the sugar moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：2309 / 2316

页数：8

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