Chiral poisoning in the kinetic resolution of allylic alcohols

J. W. Falle; Makoto Tokunaga

doi:10.1016/S0040-4039(00)60125-9

Chiral poisoning in the kinetic resolution of allylic alcohols

J. W. Falle, Makoto Tokunaga

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

47 Citations (Scopus)

Abstract

Recently, hydrogenations of allylic alcohols using ruthenium catalysts with enantiomerically pure phosphines, such as (R)-BINAP were reported to be useful for the kinetic resolution of cyclic allylic alcohols. These kinetic resolutions can also be effected using racemic BINAP and preferentially deactivating one enantiomer of the catalyst with an enantiomerically pure chiral poison. Poisoning of racemic (BINAP)-RuCl₂ (dmf)_x with (1R,2S)-ephedrine provided (R)-2-cyclohexenol in 93% ee at 72% conversion.

Original language	English
Pages (from-to)	7359-7362
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(00)60125-9
Publication status	Published - Nov 12 1993
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)60125-9

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title = "Chiral poisoning in the kinetic resolution of allylic alcohols",

abstract = "Recently, hydrogenations of allylic alcohols using ruthenium catalysts with enantiomerically pure phosphines, such as (R)-BINAP were reported to be useful for the kinetic resolution of cyclic allylic alcohols. These kinetic resolutions can also be effected using racemic BINAP and preferentially deactivating one enantiomer of the catalyst with an enantiomerically pure chiral poison. Poisoning of racemic (BINAP)-RuCl2 (dmf)x with (1R,2S)-ephedrine provided (R)-2-cyclohexenol in 93% ee at 72% conversion.",

author = "Falle, {J. W.} and Makoto Tokunaga",

note = "Funding Information: We thank the National Science Foundation for supporto f this research.",

year = "1993",

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doi = "10.1016/S0040-4039(00)60125-9",

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T1 - Chiral poisoning in the kinetic resolution of allylic alcohols

AU - Falle, J. W.

AU - Tokunaga, Makoto

N1 - Funding Information: We thank the National Science Foundation for supporto f this research.

PY - 1993/11/12

Y1 - 1993/11/12

N2 - Recently, hydrogenations of allylic alcohols using ruthenium catalysts with enantiomerically pure phosphines, such as (R)-BINAP were reported to be useful for the kinetic resolution of cyclic allylic alcohols. These kinetic resolutions can also be effected using racemic BINAP and preferentially deactivating one enantiomer of the catalyst with an enantiomerically pure chiral poison. Poisoning of racemic (BINAP)-RuCl2 (dmf)x with (1R,2S)-ephedrine provided (R)-2-cyclohexenol in 93% ee at 72% conversion.

AB - Recently, hydrogenations of allylic alcohols using ruthenium catalysts with enantiomerically pure phosphines, such as (R)-BINAP were reported to be useful for the kinetic resolution of cyclic allylic alcohols. These kinetic resolutions can also be effected using racemic BINAP and preferentially deactivating one enantiomer of the catalyst with an enantiomerically pure chiral poison. Poisoning of racemic (BINAP)-RuCl2 (dmf)x with (1R,2S)-ephedrine provided (R)-2-cyclohexenol in 93% ee at 72% conversion.

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DO - 10.1016/S0040-4039(00)60125-9

M3 - Article

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SN - 0040-4039

VL - 34

SP - 7359

EP - 7362

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Chiral poisoning in the kinetic resolution of allylic alcohols

Abstract

All Science Journal Classification (ASJC) codes

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