Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

Andrew David Smith; Alyn Davies; Alexandra Martha Zoya Slawin

doi:10.1002/chem.201504256

Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

Andrew David Smith, Alyn Davies, Alexandra Martha Zoya Slawin

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

Abstract

The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.

Original language	English
Pages (from-to)	18944–18948
Journal	Chemistry - A European Journal
Volume	21
Issue number	52
Early online date	26 Oct 2015
DOIs	https://doi.org/10.1002/chem.201504256
Publication status	Published - 14 Dec 2015

Keywords

Organocatalysis
Lewis-base
N-heterocyclic carbene
Pentafluoroethyl
Oxetane

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10.1002/chem.201504256

Smith_2015_CEJ_Enantioselective_AM
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://dx.doi.org/10.1002/chem.201504256
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title = "Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes",

abstract = "The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.",

keywords = "Organocatalysis, Lewis-base, N-heterocyclic carbene, Pentafluoroethyl, Oxetane",

author = "Smith, {Andrew David} and Alyn Davies and Slawin, {Alexandra Martha Zoya}",

note = "The authors thank the Royal Society for a University Research Fellowship (A.D.S.), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.). ",

year = "2015",

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day = "14",

doi = "10.1002/chem.201504256",

language = "English",

volume = "21",

pages = "18944–18948",

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T1 - Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

AU - Smith, Andrew David

AU - Davies, Alyn

AU - Slawin, Alexandra Martha Zoya

N1 - The authors thank the Royal Society for a University Research Fellowship (A.D.S.), and the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no. 279850 (A.T.D.).

PY - 2015/12/14

Y1 - 2015/12/14

N2 - The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.

AB - The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.

KW - Organocatalysis

KW - Lewis-base

KW - N-heterocyclic carbene

KW - Pentafluoroethyl

KW - Oxetane

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DO - 10.1002/chem.201504256

M3 - Article

SN - 0947-6539

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SP - 18944

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 52

ER -

Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

Abstract

Keywords

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Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

Developing α-aroyloxyaldehydes as azolium enolate precursors in N-heterocyclic carbene organocatalysis

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Enantioselective NHC-catalyzed redox [2+2] cycloadditions with perfluoroketones; a route to fluorinated oxetanes

Abstract

Keywords

Access to Document

Other files and links

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Projects

Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

Student theses

Developing α-aroyloxyaldehydes as azolium enolate precursors in N-heterocyclic carbene organocatalysis

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