A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives.

被引：50

作者：

Allin, SM ^{[1
]}

Northfield, CJ ^{[1
]}

Page, MI ^{[1
]}

Slawin, AMZ ^{[1
]}

机构：

[1] UNIV HUDDERSFIELD,DEPT CHEM & BIOL SCI,HUDDERSFIELD HD1 3DH,W YORKSHIRE,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(97)00686-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic gamma-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives. (C) 1997 Elsevier Science Ltd.

引用

页码：3627 / 3630

页数：4

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