Asymmetric hetero-Diels-Alder reactions. Mechanism of the reaction of alkenyloxazolines with isocyanates

被引：15

作者：

Elliott, MC ^{[1
]}

Kruiswijk, E ^{[1
]}

Willock, DJ ^{[1
]}

机构：

[1] Univ Wales Coll Cardiff, Dept Chem, Cardiff CF1 3TB, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric synthesis; Diels-Alder reactions;

D O I：

10.1016/S0040-4039(98)01949-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereomerically pure oxazolo[3,2-c]pyrimidines can be readily prepared by the reaction of alkenyloxazolines with isocyanates. These compounds undergo epimerisation upon prolonged heating. The mechanism of this transformation has been investigated experimentally and computationally. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：8911 / 8914

页数：4

共 4 条

[1] Highly diastereoselective hetero-Diels-Alder reactions of alkenyidihydrooxazoles as an approach to novel pyrimidine derivatives [J].

Elliot, MC ;

Kruiswijk, E .

CHEMICAL COMMUNICATIONS, 1997, (23) :2311-2312

[2]

ELLIOTT MC, 1998, IN PRESS J CHEM CRYS

[3] SEMIEMPIRICAL CALCULATIONS ON HETEROCUMULENE-HETERODIENE CYCLOADDITION REACTIONS - KETENE PLUS 1-AZABUTADIENE [J].

FABIAN, WMF ;

KOLLENZ, G .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1994, 7 (01) :1-8

[4]

Tietze LF, 1997, TOP CURR CHEM, V189, P1

← 1 →