Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents

Pablo Ortiz; Juan F. Collados; Ravindra P. Jumde; Edwin Otten; Syuzanna R. Harutyunyan

doi:10.1002/anie.201609963

Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents

Pablo Ortiz
, Juan F. Collados
, Ravindra P. Jumde
, Edwin Otten
, Syuzanna R. Harutyunyan^*

^*Corresponding author for this work

Bioeconomy and CO2

University of Groningen

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

26 Citations (Scopus)

Abstract

Inexpensive and readily available organomagnesium reagents were used for the catalytic enantioselective alkylation of enolizable N-sulfonyl ketimines. The low reactivity and competing enolization of the ketimines was overcome by the use of a copper–phosphine chiral catalyst, which also rendered the transformation highly chemoselective and enantioselective for a broad range of ketimine substrates.

Original language	English
Pages (from-to)	3041-3044
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	11
DOIs	https://doi.org/10.1002/anie.201609963
Publication status	Published - 6 Mar 2017

Keywords

Grignard reagents
alkylation
asymmetric catalysis
copper catalysis
enolizable ketimines

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10.1002/anie.201609963

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title = "Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents",

abstract = "Inexpensive and readily available organomagnesium reagents were used for the catalytic enantioselective alkylation of enolizable N-sulfonyl ketimines. The low reactivity and competing enolization of the ketimines was overcome by the use of a copper–phosphine chiral catalyst, which also rendered the transformation highly chemoselective and enantioselective for a broad range of ketimine substrates.",

keywords = "Grignard reagents, alkylation, asymmetric catalysis, copper catalysis, enolizable ketimines",

author = "Pablo Ortiz and Collados, \{Juan F.\} and Jumde, \{Ravindra P.\} and Edwin Otten and Harutyunyan, \{Syuzanna R.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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T1 - Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents

AU - Ortiz, Pablo

AU - Collados, Juan F.

AU - Jumde, Ravindra P.

AU - Otten, Edwin

AU - Harutyunyan, Syuzanna R.

PY - 2017/3/6

Y1 - 2017/3/6

N2 - Inexpensive and readily available organomagnesium reagents were used for the catalytic enantioselective alkylation of enolizable N-sulfonyl ketimines. The low reactivity and competing enolization of the ketimines was overcome by the use of a copper–phosphine chiral catalyst, which also rendered the transformation highly chemoselective and enantioselective for a broad range of ketimine substrates.

AB - Inexpensive and readily available organomagnesium reagents were used for the catalytic enantioselective alkylation of enolizable N-sulfonyl ketimines. The low reactivity and competing enolization of the ketimines was overcome by the use of a copper–phosphine chiral catalyst, which also rendered the transformation highly chemoselective and enantioselective for a broad range of ketimine substrates.

KW - Grignard reagents

KW - alkylation

KW - asymmetric catalysis

KW - copper catalysis

KW - enolizable ketimines

UR - https://www.scopus.com/pages/publications/85014518811

U2 - 10.1002/anie.201609963

DO - 10.1002/anie.201609963

M3 - Article

C2 - 28156047

AN - SCOPUS:85014518811

SN - 1433-7851

VL - 56

SP - 3041

EP - 3044

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents

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Keywords

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