Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

P J Black, K Jenkins, J M J Williams

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14 Citations (Scopus)

Abstract

The asymmetric epoxidation of allylic cyanohydrins using the Sharpless kinetic resolution (SKR) reaction was explored. The SKR methodology was extended to enals via in-situ conversion into the corresponding cyanohydrin. The prospect of achieving a dynamic Sharpless kinetic resolution was investigated and the enantioselectivity of the SKR of (E)-2-hydroxy-3-methyl-4-phenyl-3-butenenitrile 1 studied. Reversible hydrocyanation of alpha-methyl cinnamaldehyde was developed and a one-pot hydrocyanation/epoxidation process achieved. (C) 2002 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)317-323
Number of pages7
JournalTetrahedron: Asymmetry
Volume13
Issue number3
Publication statusPublished - 2002

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    Black, P. J., Jenkins, K., & Williams, J. M. J. (2002). Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals. Tetrahedron: Asymmetry, 13(3), 317-323.