Heterosubstituted chlorohydrins:: Knoevenagel reaction versus epoxide formation

被引：10

作者：

Florio, S

Troisi, L

Capriati, V

Coletta, G

机构：

[1] Univ Bari, Fac Farm, Dipartimento Farmacochim, CNR,Ctr Studio Metodol Innovat Sintesi Organ, I-70125 Bari, Italy

[2] Univ Lecce, Dipartimento Biol, I-73100 Lecce, Italy

来源：

TETRAHEDRON | 1999年 / 55卷 / 32期

关键词：

heterosubstituted chlorohydrin; chloroalkene; Knoevenagel reaction; Darzens condensation; epoxide formation;

D O I：

10.1016/S0040-4020(99)00525-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiated chloromethyl derivatives 2a-d, available by deprotonation of 2-(chloromethyl)-1,3-benzothiazole 1a -1,3-oxazoIine 1b, -pyridine 1c and -quinoline 1d, react with carbonyl compounds to give chlorohydrins 3a-g and then epoxides 4a-g upon treatment with NaOH/(PrOH)-Pr-i. The same chlorohydrins 3a-g could be converted into heterosubstituted chloroalkenes 5a-g with very high E stereoselection upon reaction with MeSO2Cl/Et3N. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：9859 / 9866

页数：8

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