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

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

439 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

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.5b13211

Cite this

@article{548e4a84b8e84d7d92a9cd129afd357a,

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 = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = feb,

day = "17",

doi = "10.1021/jacs.5b13211",

language = "English (US)",

volume = "138",

pages = "1832--1835",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis

AU - Zuo, Zhiwei

AU - Cong, Huan

AU - Li, Wei

AU - Choi, Junwon

AU - Fu, Gregory C.

AU - MacMillan, David W.C.

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.

UR - http://www.scopus.com/inward/record.url?scp=84959018638&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84959018638&partnerID=8YFLogxK

U2 - 10.1021/jacs.5b13211

DO - 10.1021/jacs.5b13211

M3 - Article

C2 - 26849354

AN - SCOPUS:84959018638

SN - 0002-7863

VL - 138

SP - 1832

EP - 1835

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 6

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this