Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes

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

doi:10.1021/ol402955f

Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes

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

^*Corresponding author for this work

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

Abstract

Asymmetric alpha-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of alpha-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form alpha-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
DOIs	https://doi.org/10.1021/ol402955f
Publication status	Published - 6 Dec 2013

Keywords

DIELS-ALDER REACTIONS
N-HETEROCYCLIC CARBENES
CARBONYL-COMPOUNDS
AMINO-ACIDS
ENANTIOSELECTIVE SYNTHESIS
4+2 CYCLOADDITION
ARYL HALIDES
ALDEHYDES
ACTIVATION
ESTERS

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10.1021/ol402955f

Clean catalysis for sustainable develop: Clean catalysis for sustainable development
Kamer, P. C. J. (PI)
EPSRC
1/11/12 → 31/10/17
Project: Standard

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@article{7ee242ce2520424ea16e90b3f070b6a1,

title = "Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes",

abstract = "Asymmetric alpha-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of alpha-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form alpha-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.",

keywords = "DIELS-ALDER REACTIONS, N-HETEROCYCLIC CARBENES, CARBONYL-COMPOUNDS, AMINO-ACIDS, ENANTIOSELECTIVE SYNTHESIS, 4+2 CYCLOADDITION, ARYL HALIDES, ALDEHYDES, ACTIVATION, ESTERS",

author = "Taylor, {James E.} and Daniels, {David S. B.} and Smith, {Andrew D.}",

year = "2013",

month = dec,

day = "6",

doi = "10.1021/ol402955f",

language = "English",

volume = "15",

pages = "6058--6061",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "23",

}

TY - JOUR

T1 - Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes

AU - Taylor, James E.

AU - Daniels, David S. B.

AU - Smith, Andrew D.

PY - 2013/12/6

Y1 - 2013/12/6

N2 - Asymmetric alpha-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of alpha-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form alpha-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 alpha-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of alpha-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form alpha-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.

KW - DIELS-ALDER REACTIONS

KW - N-HETEROCYCLIC CARBENES

KW - CARBONYL-COMPOUNDS

KW - AMINO-ACIDS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - 4+2 CYCLOADDITION

KW - ARYL HALIDES

KW - ALDEHYDES

KW - ACTIVATION

KW - ESTERS

U2 - 10.1021/ol402955f

DO - 10.1021/ol402955f

M3 - Article

SN - 1523-7060

VL - 15

SP - 6058

EP - 6061

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes

Abstract

Keywords

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Clean catalysis for sustainable develop: Clean catalysis for sustainable development

Cite this