Nickel-catalyzed enantioselective arylation of pyridinium ions: Harnessing an iminium ion activation mode

Stephen T. Chau; J. Patrick Lutz; Kevin Wu; Abigail G. Doyle

doi:10.1002/anie.201303994

Nickel-catalyzed enantioselective arylation of pyridinium ions: Harnessing an iminium ion activation mode

Stephen T. Chau, J. Patrick Lutz, Kevin Wu, Abigail G. Doyle

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

72 Scopus citations

Abstract

A nickel for your thoughts.ï̧ An enantioselective nickel-catalyzed cross-coupling between N-acylpyridinium salts and organozinc reagents is reported. The catalytic system, which is comprised of an air-stable Ni^II source and a chiral phosphoramidite ligand, affords 2-substituted-2,3-dihydro-4-pyridones with up to >99 % ee.

Original language	English (US)
Pages (from-to)	9153-9156
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	35
DOIs	https://doi.org/10.1002/anie.201303994
State	Published - Aug 26 2013

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Negishi reaction
asymmetric catalysis
cross-coupling
nickel
nitrogen heterocycles

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author = "Chau, {Stephen T.} and Lutz, {J. Patrick} and Kevin Wu and Doyle, {Abigail G.}",

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AU - Chau, Stephen T.

AU - Lutz, J. Patrick

AU - Wu, Kevin

AU - Doyle, Abigail G.

PY - 2013/8/26

Y1 - 2013/8/26

N2 - A nickel for your thoughts.ï̧ An enantioselective nickel-catalyzed cross-coupling between N-acylpyridinium salts and organozinc reagents is reported. The catalytic system, which is comprised of an air-stable NiII source and a chiral phosphoramidite ligand, affords 2-substituted-2,3-dihydro-4-pyridones with up to >99 % ee.

AB - A nickel for your thoughts.ï̧ An enantioselective nickel-catalyzed cross-coupling between N-acylpyridinium salts and organozinc reagents is reported. The catalytic system, which is comprised of an air-stable NiII source and a chiral phosphoramidite ligand, affords 2-substituted-2,3-dihydro-4-pyridones with up to >99 % ee.

KW - Negishi reaction

KW - asymmetric catalysis

KW - cross-coupling

KW - nickel

KW - nitrogen heterocycles

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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ER -

Nickel-catalyzed enantioselective arylation of pyridinium ions: Harnessing an iminium ion activation mode

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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