DIASTEREOSELECTIVE SYNTHESIS OF (1S,2S,3R,6S) -CHLORO-3-METHYL-6-ISOPROPENYL-1,2-CYCLOHEXANEDIOL VIA PRINS REACTION INDUCED BY ZINC AND TRIMETHYLSILYL CHLORIDE

Authors
MARTY M STOECKLIEVANS H NEIER R
Citation
M. Marty et al., DIASTEREOSELECTIVE SYNTHESIS OF (1S,2S,3R,6S) -CHLORO-3-METHYL-6-ISOPROPENYL-1,2-CYCLOHEXANEDIOL VIA PRINS REACTION INDUCED BY ZINC AND TRIMETHYLSILYL CHLORIDE, Tetrahedron, 52(13), 1996, pp. 4645-4658
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
13
Year of publication
1996
Pages
4645 - 4658
Database
ISI
SICI code
0040-4020(1996)52:13<4645:DSO(->2.0.ZU;2-T
Abstract
While attempting to synthesize a potential inhibitor of the biosynthet ic step of formation of PEG, a novel catalytic system inducing the Pri ns reaction was discovered. Treatment of epoxy geranial with Zn and tr imethylsilyl chloride gave (1S,2S,3R,6S) -Chloro-3-methyl-6-isopropeny l-1,2-cyclohexanediol in high diastereoselcctivity.