Proton abstraction and electrophilic quench at C-2 of imidazolidines

被引：8

作者：

Coldham, I

Judkins, RA

Witty, DR

机构：

[1] Univ Exeter, Dept Chem, Exeter EX4 4QD, Devon, England

[2] SmithKline Beecham Pharmaceut, Harlow CM19 5AW, Essex, England

来源：

TETRAHEDRON | 1998年 / 54卷 / 47期

关键词：

D O I：

10.1016/S0040-4020(98)00877-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazolidines bearing tert-butoxycarbonyl groups on both nitrogen atoms have been prepared in order to test their ability to act as acyl anion equivalents. Proton abstraction was achieved successfully at C-2, between the two nitrogen atoms, using the base sec-butyllithium. The resulting organolithium was trapped with a variety of electrophiles. The imidazolidine can be cleaved with acid to generate the desired carbonyl compound. Using chiral imidazolidines and aldehyde electrophiles, the carbon-carbon bond formation occurred with low diastereoselectivities. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：14255 / 14264

页数：10

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