ASYMMETRIC DIHYDROXYLATION OF PRIMARY ALLYLIC HALIDES AND A CONCISE SYNTHESIS OF (-)-DIEPOXYBUTANE

Authors
VANHESSCHE KPM WANG ZM SHARPLESS KB
Citation
Kpm. Vanhessche et al., ASYMMETRIC DIHYDROXYLATION OF PRIMARY ALLYLIC HALIDES AND A CONCISE SYNTHESIS OF (-)-DIEPOXYBUTANE, Tetrahedron letters, 35(21), 1994, pp. 3469-3472
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
21
Year of publication
1994
Pages
3469 - 3472
Database
ISI
SICI code
0040-4039(1994)35:21<3469:ADOPAH>2.0.ZU;2-8
Abstract
Tire asymmetric dihydroxylation (AD) of primary allylic halides is des cribed. Enantiomeric excesses range from 40 to 98%. Subsequent base tr eatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (-)-diepoxybutane, an important C-4-ch iral building block.