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
收藏
页码：12101 / 12110
页数：10
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