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Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals


Reference:

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

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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.

Details

Item Type Articles
CreatorsBlack, P. J., Jenkins, K. and Williams, J. M. J.
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code5163
Additional InformationID number: ISI:000175140700015

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