α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

被引：20

作者：

Synofzik, Judith ^{[1
]}

Dar'in, Dmitry ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Kantin, Grigory ^{[1
]}

Bakulina, Olga ^{[1
]}

Krasavin, Mikhail ^{[1
]}

机构：

[1] St Petersburg State Univ, St Petersburg 199034, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

基金：

俄罗斯基础研究基金会;

关键词：

CASTAGNOLI-CUSHMAN REACTION; PRODUCT SPACE; CYCLOADDITION; ACYLKETENES; IMINES;

D O I：

10.1021/acs.joc.9b02030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thermally promoted reaction of alpha-acyl-alpha-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers alpha-alkoxycarbonyl-substituted beta-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of beta-lactams.

引用

页码：12101 / 12110

页数：10

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