Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis

Zhiwei Zuo; Huan Cong; Wei Li; Junwon Choi; Gregory C. Fu; David W.C. MacMillan

doi:10.1021/jacs.5b13211

Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis

Zhiwei Zuo, Huan Cong, Wei Li, Junwon Choi, Gregory C. Fu, David W.C. MacMillan

Chemistry

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

368 Scopus citations

Abstract

An asymmetric decarboxylative C_sp₃_-Csp² cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant α-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.

Original language	English (US)
Pages (from-to)	1832-1835
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	138
Issue number	6
DOIs	https://doi.org/10.1021/jacs.5b13211
State	Published - Feb 17 2016

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.5b13211

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title = "Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis",

abstract = "An asymmetric decarboxylative Csp3-Csp2 cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant α-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.",

author = "Zhiwei Zuo and Huan Cong and Wei Li and Junwon Choi and Fu, {Gregory C.} and MacMillan, {David W.C.}",

note = "Funding Information: Financial support was provided by the NIH (NIGMS R01 GM093213 and R01 GM062871) and by gifts from Merck and Amgen. Z.Z. is grateful for a postdoctoral fellowship from the Shanghai Institute of Organic Chemistry. Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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AU - Zuo, Zhiwei

AU - Cong, Huan

AU - Li, Wei

AU - Choi, Junwon

AU - Fu, Gregory C.

AU - MacMillan, David W.C.

N1 - Funding Information: Financial support was provided by the NIH (NIGMS R01 GM093213 and R01 GM062871) and by gifts from Merck and Amgen. Z.Z. is grateful for a postdoctoral fellowship from the Shanghai Institute of Organic Chemistry. Publisher Copyright: © 2016 American Chemical Society.

PY - 2016/2/17

Y1 - 2016/2/17

N2 - An asymmetric decarboxylative Csp3-Csp2 cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant α-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.

AB - An asymmetric decarboxylative Csp3-Csp2 cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant α-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.

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Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis

Abstract

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