Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

Julia A. Kalow; Abigail G. Doyle

doi:10.1021/ja100161d

Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

Julia A. Kalow, Abigail G. Doyle

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

229 Scopus citations

Abstract

(Figure Presented) An enantioselective method for the synthesis of β-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with k_rel values as high as 300.

Original language	English (US)
Pages (from-to)	3268-3269
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	132
Issue number	10
DOIs	https://doi.org/10.1021/ja100161d
State	Published - Mar 17 2010

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja100161d

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title = "Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system",

abstract = "(Figure Presented) An enantioselective method for the synthesis of β-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with krel values as high as 300.",

author = "Kalow, {Julia A.} and Doyle, {Abigail G.}",

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AU - Kalow, Julia A.

AU - Doyle, Abigail G.

PY - 2010/3/17

Y1 - 2010/3/17

N2 - (Figure Presented) An enantioselective method for the synthesis of β-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with krel values as high as 300.

AB - (Figure Presented) An enantioselective method for the synthesis of β-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with krel values as high as 300.

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Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system

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