Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents

Pablo Ortiz; Juan Collados Lujan; 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 Collados Lujan, Ravindra P Jumde, Edwin Otten, Syuzanna R Harutyunyan

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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 - 2017

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Journal Article

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10.1002/anie.201609963

Ortiz_et_al-2017-Angewandte_Chemie_International_EditionFinal publisher's version, 644 KBLicence: Taverne

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CCDC 1509347: Experimental Crystal Structure Determination
Ortiz, P. (Contributor), Collados Lujan, J. (Contributor), Jumde, R. P. (Contributor), Otten, E. (Contributor) & Harutyunyan, S. (Contributor), University of Groningen, 11-Oct-2016
DOI: 10.5517/ccdc.csd.cc1mnlmh
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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.",

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AU - Ortiz, Pablo

AU - Collados Lujan, Juan

AU - Jumde, Ravindra P

AU - Otten, Edwin

AU - Harutyunyan, Syuzanna R

PY - 2017

Y1 - 2017

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 - Journal Article

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DO - 10.1002/anie.201609963

M3 - Article

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SN - 1521-3773

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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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CCDC 1509347: Experimental Crystal Structure Determination

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