Selectivities in the reaction of vicinal diimines and acyl chlorides

被引：26

作者：

Wang, Zhixin ^{[1
]}

Chen, Ning ^{[1
]}

Xu, Jiaxi ^{[1
,2
]}

机构：

[1] Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Dept Organ Chem, Fac Sci, Beijing 100029, Peoples R China

[2] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Peoples R China

来源：

TETRAHEDRON | 2011年 / 67卷 / 50期

基金：

中国国家自然科学基金; 北京市自然科学基金;

关键词：

Chemoselectivity; Diastereoselectivity; Diimine; Regioselectivity; Staudinger reaction; N-CARBOXY ANHYDRIDES; BETA-LACTAM; STAUDINGER REACTION; ASYMMETRIC-SYNTHESIS; RING EXPANSION; STEREOSELECTIVE-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; SUCCINIMIDE DERIVATIVES; BUILDING-BLOCKS; AMINO-ACIDS;

D O I：

10.1016/j.tet.2011.10.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of vicinal diimines and acyl chlorides in the presence of triethylamine produces 3-imino-beta-lactams and/or bis-beta-lactams chemo-, regio-, and stereoselectively, which are important intermediates in pharmaceutical and organic synthesis. The selectivities in the reaction have been investigated. The results indicate that all diimines react with various ketenes generated from acyl chlorides in the presence of triethylamine to give rise to cis-4-imino-beta-lactams (mono-cis-beta-lactams) diastereoselectively due to the electron-withdrawing property of the imino group in the vicinal diimines. Bis-beta-lactams were obtained from diimines via the mono-cis-beta-lactams as intermediates. Only ketenes with strong electron-donating substituents can react with the mono-cis-beta-lactams to yield bis-beta-lactams, affording a pair of C2-symmetric cis-bis-beta-lactams with symmetric diimines, two or four pairs of diastereomeric bis-beta-lactams with ketoaldehyde-derived unsymmetric diimines depending on the steric hindrance of their N-substituents. The current investigation provides very important information for the selective preparation of mono- and bis-beta-lactams from vicinal diimines. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：9690 / 9699

页数：10

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