Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

Brian P. Woods; Manuel Orlandi; Chung Yang Huang; Matthew S. Sigman; Abigail G. Doyle

doi:10.1021/jacs.7b03448

Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

Brian P. Woods, Manuel Orlandi, Chung Yang Huang, Matthew S. Sigman, Abigail G. Doyle

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

205 Scopus citations

Abstract

A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.

Original language	English (US)
Pages (from-to)	5688-5691
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	139
Issue number	16
DOIs	https://doi.org/10.1021/jacs.7b03448
State	Published - Apr 26 2017

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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title = "Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines",

abstract = "A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.",

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AU - Woods, Brian P.

AU - Orlandi, Manuel

AU - Huang, Chung Yang

AU - Sigman, Matthew S.

AU - Doyle, Abigail G.

PY - 2017/4/26

Y1 - 2017/4/26

N2 - A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.

AB - A Ni-catalyzed reductive cross-coupling of styrenyl aziridines with aryl iodides is reported. This reaction proceeds by a stereoconvergent mechanism and is thus amenable to asymmetric catalysis using a chiral bioxazoline ligand for Ni. The process allows facile access to highly enantioenriched 2-arylphenethylamines from racemic aziridines. Multivariate analysis revealed that ligand polarizability, among other features, influences the observed enantioselectivity, shedding light on the success of this emerging ligand class for enantioselective Ni catalysis.

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Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines

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