Tetrahedron: Asymmetry

Asymmetric synthesis of 2-substituted butane-1, 4-diols by hydrogenation of homochiral fumaramide derivatives

S Jawaid, LJ Farrugia, DJ Robins

Index: Jawaid, Samaila; Farrugia, Louis J.; Robins, David J. Tetrahedron Asymmetry, 2004 , vol. 15, # 24 p. 3979 - 3988

Full Text: HTML

Citation Number: 13

Abstract

Diastereoselective hydrogenation of homochiral fumaramides 1 derived from (2R)- Oppolzer's sultam was observed by analysis of the 1H NMR spectra of the succinamide mixtures with de's of 77–88%. Reduction of these succinamides using LiAlH4 gave the corresponding (2S)-butane-1, 4-diols and established that addition of hydrogen takes place selectively on the re-face of fumaramides 1. The stereoselectivity was confirmed by ...