Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

P J Black, K Jenkins, J M J Williams

Research output: Contribution to journalArticle

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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epoxidation
Epoxidation
Chemical activation
activation
Kinetics
kinetics
electronics
Enantioselectivity
methodology
cyanohydrin

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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.

Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals. / Black, P J; Jenkins, K; Williams, J M J.

In: Tetrahedron: Asymmetry, Vol. 13, No. 3, 2002, p. 317-323.

Research output: Contribution to journalArticle

Black, PJ, Jenkins, K & Williams, JMJ 2002, 'Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals', Tetrahedron: Asymmetry, vol. 13, no. 3, pp. 317-323.
Black, P J ; Jenkins, K ; Williams, J M J. / Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals. In: Tetrahedron: Asymmetry. 2002 ; Vol. 13, No. 3. pp. 317-323.
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