Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

P J Black; K Jenkins; J M J Williams

doi:10.1016/s0957-4166(02)00100-3

Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

P J Black, K Jenkins, J M J Williams

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

14 Citations (SciVal)

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
DOIs	https://doi.org/10.1016/s0957-4166(02)00100-3
Publication status	Published - 2002

Bibliographical note

ID number: ISI:000175140700015

Access to Document

10.1016/s0957-4166(02)00100-3

Cite this

@article{53dedccb317f4a6ea32149e9fc2a6aac,

title = "Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals",

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.",

author = "Black, \{P J\} and K Jenkins and Williams, \{J M J\}",

note = "ID number: ISI:000175140700015",

year = "2002",

doi = "10.1016/s0957-4166(02)00100-3",

language = "English",

volume = "13",

pages = "317--323",

journal = "Tetrahedron: Asymmetry",

issn = "0957-4166",

publisher = "Elsevier",

number = "3",

}

TY - JOUR

T1 - Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

AU - Black, P J

AU - Jenkins, K

AU - Williams, J M J

N1 - ID number: ISI:000175140700015

PY - 2002

Y1 - 2002

N2 - 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.

AB - 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.

U2 - 10.1016/s0957-4166(02)00100-3

DO - 10.1016/s0957-4166(02)00100-3

M3 - Article

SN - 0957-4166

VL - 13

SP - 317

EP - 323

JO - Tetrahedron: Asymmetry

JF - Tetrahedron: Asymmetry

IS - 3

ER -

Catalytic electronic activation: indirect Sharpless asymmetric epoxidation of enals

Abstract

Bibliographical note

Access to Document

Fingerprint

Cite this