Rationalising diastereoselection in the dynamic kinetic resolution of α-haloacyl imidazolidinones

被引：25

作者：

Caddick, S ^{[1
]}

Jenkins, K

Treweeke, N

Candeias, SX

Afonso, CAM

机构：

[1] Univ Sussex, Chem Lab, Ctr Biomol Design & Drug Dev, Brighton BN1 9QJ, E Sussex, England

[2] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, P-2825 Monte De Caparica, Portugal

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(98)00175-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A crossover from S(N)2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of alpha-haloacyl imidazolidinones. Aprotic nucleophiles (Nu(-)) react preferentially with the 5S*,2'R* diastereomer via an S(N)2 mechanism. Conversely, amines (R2NH) generally react preferentially with the 5S*,2'S* diastereomer. General base catalysis via a bifurcated hydrogen bonded assembly accounts for this anomalous stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2203 / 2206

页数：4

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