Heteroatom effect on potential energy topology. A novel reaction mechanism of stereospecific Staudinger synthesis

被引：3

作者：

Abranyi-Balogh, Peter ^{[1
,2
]}

Mucsi, Zoltan ^{[1
,2
]}

Csizmadia, Imre Gyula ^{[1
]}

Dancso, Andras ^{[3
]}

Kegleyich, Gyoergy ^{[2
]}

Milen, Matyas ^{[2
,3
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

[2] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary

[3] Egis Pharmaceut Plc, Div Chem Res, H-1475 Budapest, Hungary

来源：

TETRAHEDRON | 2014年 / 70卷 / 51期

关键词：

beta-Carbolines; beta-Lactams; Staudinger reaction; Stereoselectivity; Mechanism; Heteroatom effect; SUBSTITUTED BETA-LACTAMS; ASYMMETRIC-SYNTHESIS; MEISENHEIMER REARRANGEMENT; THIENOPYRIDINE DERIVATIVES; PHOTOLYTIC REACTION; KETENES; IMINES; STEREOSELECTIVITY; CYCLOADDITION; DIAZOKETONES;

D O I：

10.1016/j.tet.2014.10.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Staudinger synthesis of various beta-carbolines and thienopyridines with acetyl chloride derivatives led to novel beta-lactam-type fused heterocyclic compounds. The reaction was stereospecific, giving exclusively the cis cycloadducts as racemates. The enthalpy profile and the driving force for the cis-selectivity of this cycloaddition was studied by high level quantum chemical calculations and was assigned to a new effect of the neighbouring heteroatom of the acyl group. In the course of the reaction a new side product was formed supporting the mechanistic results. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：9682 / 9694

页数：13

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