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

Jawaid, S., Farrugia, L. J. and Robins, D. J. (2004) Asymmetric synthesis of 2-substituted butane-1,4-diols by hydrogenation of homochiral fumaramide derivatives. Tetrahedron: Asymmetry, 15(24), pp. 3979-3988. (doi: 10.1016/j.tetasy.2004.11.023)

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 estimating the ee’s from the 19F NMR spectra of the Mosher’s diesters of the diols. This methodology was applied to the synthesis of selected pyrrolidine natural products in homochiral form.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Robins, Prof David and Farrugia, Dr Louis
• Authors: Jawaid, S., Farrugia, L. J., and Robins, D. J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Tetrahedron: Asymmetry
• Publisher: Elsevier
• ISSN: 0957-4166
• ISSN (Online): 1362-511X
• Published Online: 01 December 2004