Lithiated chloromethyl derivatives 2a-d, available by deprotonation of 2-(c
hloromethyl)-1,3-benzothiazole 1a -1,3-oxazoIine 1b, -pyridine 1c and -quin
oline 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 ver
y high E stereoselection upon reaction with MeSO2Cl/Et3N. (C) 1999 Publishe
d by Elsevier Science Ltd. All rights reserved.