Heterosubstituted chlorohydrins: Knoevenagel reaction versus epoxide formation

Authors
Florio, S Troisi, L Capriati, V Coletta, G
Citation
S. Florio et al., Heterosubstituted chlorohydrins: Knoevenagel reaction versus epoxide formation, TETRAHEDRON, 55(32), 1999, pp. 9859-9866
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
32
Year of publication
1999
Pages
9859 - 9866
Database
ISI
SICI code
0040-4020(19990806)55:32<9859:HCKRVE>2.0.ZU;2-R
Abstract
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.