Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

P J Black, K Jenkins, J M J Williams

Research output: Contribution to journal › Article

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

Cite this

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 journal › Article

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 PJ, Jenkins K, Williams JMJ. Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals. Tetrahedron: Asymmetry. 2002;13(3):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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