Asymmetric epoxidation of cis-alkenes mediated by iminium salts: Highly enantioselective synthesis of levcromakalim

P. C. B. Bulman Page; B. R. Buckley; H. Heaney; A. J. Blacker

doi:10.1021/ol047836h

Asymmetric epoxidation of cis-alkenes mediated by iminium salts: Highly enantioselective synthesis of levcromakalim

P. C. B. Bulman Page, B. R. Buckley, H. Heaney, A. J. Blacker

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

89 Citations (Scopus)

Abstract

A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric oxidant, giving ee's of up to 97%. The reaction has been used as the key step in an enantioselertive synthesis of the antihypertensive agent levcromakalim.

Original language	English
Pages (from-to)	375-377
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	3
DOIs	https://doi.org/10.1021/ol047836h
Publication status	Published - 2005

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10.1021/ol047836h

Cite this

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title = "Asymmetric epoxidation of cis-alkenes mediated by iminium salts: Highly enantioselective synthesis of levcromakalim",

abstract = "A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric oxidant, giving ee's of up to 97%. The reaction has been used as the key step in an enantioselertive synthesis of the antihypertensive agent levcromakalim.",

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journal = "Organic Letters",

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AU - Bulman Page, P. C. B.

AU - Buckley, B. R.

AU - Heaney, H.

AU - Blacker, A. J.

PY - 2005

Y1 - 2005

N2 - A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric oxidant, giving ee's of up to 97%. The reaction has been used as the key step in an enantioselertive synthesis of the antihypertensive agent levcromakalim.

AB - A range of cis-substituted olefins has been epoxidized with a new dihydroisoquinolinium salt catalyst, using tetraphenylphosphonium monoperoxysulfate as the stoichiometric oxidant, giving ee's of up to 97%. The reaction has been used as the key step in an enantioselertive synthesis of the antihypertensive agent levcromakalim.

U2 - 10.1021/ol047836h

DO - 10.1021/ol047836h

M3 - Article

SN - 1523-7060

VL - 7

SP - 375

EP - 377

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -