Asymmetric NHC-catalyzed redox α-amination of α- aroyloxyaldehydes

James E. Taylor; David S.B. Daniels; Andrew D. Smith

doi:10.1021/ol402955f

Asymmetric NHC-catalyzed redox α-amination of α- aroyloxyaldehydes

James E. Taylor, David S.B. Daniels, Andrew D. Smith

Department of Chemistry

University of St Andrews

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

55 Citations (SciVal)

Abstract

Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.

Original language	English
Pages (from-to)	6058-6061
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	23
Early online date	11 Nov 2013
DOIs	https://doi.org/10.1021/ol402955f
Publication status	Published - 6 Dec 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol402955f

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title = "Asymmetric NHC-catalyzed redox α-amination of α- aroyloxyaldehydes",

abstract = "Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99\% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.",

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AU - Daniels, David S.B.

AU - Smith, Andrew D.

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Y1 - 2013/12/6

N2 - Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.

AB - Asymmetric α-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.

UR - https://www.scopus.com/pages/publications/84890043528

U2 - 10.1021/ol402955f

DO - 10.1021/ol402955f

M3 - Article

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AN - SCOPUS:84890043528

SN - 1523-7060

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EP - 6061

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Asymmetric NHC-catalyzed redox α-amination of α- aroyloxyaldehydes

Abstract

ASJC Scopus subject areas

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