ENANTIOSELECTIVE SYNTHESIS OF 2-BENZOTHIAZOLYL OXIRANES

Authors
FLORIO S CAPRIATI V RUSSO V
Citation
S. Florio et al., ENANTIOSELECTIVE SYNTHESIS OF 2-BENZOTHIAZOLYL OXIRANES, Tetrahedron letters, 38(33), 1997, pp. 5843-5846
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
33
Year of publication
1997
Pages
5843 - 5846
Database
ISI
SICI code
0040-4039(1997)38:33<5843:ESO2O>2.0.ZU;2-7
Abstract
Lithiation of 2-(chloroethyl)benzothiazole la gives (benzothiazolylchl oroethyl)lithium Ib. The reaction of Ib with ketones in the presence o f (-)-sparteine leads to chlorohydrins 2a-c that cyclize to epoxides 3 a-c, enantioselectively, the enantiomeric enrichment being dependent u pon the solvent, the lithiating agent, the reaction time. The reaction with aldehydes furnishes chlorohydrins 2d-g and then epoxides 3d-g di astereo-and enantioselectively. (C) 1997 Elsevier Science Ltd.