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 language | English |
|---|---|
| Pages (from-to) | 317-323 |
| Number of pages | 7 |
| Journal | Tetrahedron: Asymmetry |
| Volume | 13 |
| Issue number | 3 |
| Publication status | Published - 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.