Asymmetric dihydroxylation of primary allylic halides and a concise synthesis of (−)-diepoxybutane
KPM Vanhessche, ZM Wang, KB Sharpless
Index: Vanhessche, Koen P. M.; Wang, Zhi-Min; Sharpless, K. Barry Tetrahedron Letters, 1994 , vol. 35, # 21 p. 3469 - 3472
Full Text: HTML
Citation Number: 59
Abstract
Abstract The asymmetric dihydroxylation (AD) of primary allylic halides is described. Enantiomeric excesses range from 40 to 98%. Subsequent base treatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (−)- diepoxybutane, an important C 4-chiral building block.
Related Articles:
Regioncontrolled formation of iodohy dnns and expoxides from Vic-diols
[Adiyaman; Khanapure; Hwang; Rokach Tetrahedron Letters, 1995 , vol. 36, # 41 p. 7367 - 7370]
[Journal of the American Chemical Society, , vol. 127, # 41 p. 14355 - 14365]
Synthesis of chiral nonracemic diols via nucleophilic opening of (S, S)-1, 2, 3, 4-diepoxybutane
[Tetrahedron Letters, , vol. 32, # 7 p. 883 - 886]