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

Zuo, Zhiwei and Cong, Huan and Li, Wei and Choi, Junwon and Fu, Gregory C. and MacMillan, David W. C. (2016) Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis. Journal of the American Chemical Society, 138 (6). pp. 1832-1835. ISSN 0002-7863. PMCID PMC4862596. doi:10.1021/jacs.5b13211. https://resolver.caltech.edu/CaltechAUTHORS:20160216-091421574

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Abstract

An asymmetric decarboxylative C_(sp)^3–C_(sp)^2 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.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/jacs.5b13211	DOI	Article
http://pubs.acs.org/doi/suppl/10.1021/jacs.5b13211	Publisher	Supporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862596/	PubMed Central	Article

ORCID:

Author	ORCID
Li, Wei	0000-0003-2543-2558
Choi, Junwon	0000-0001-6004-5524
Fu, Gregory C.	0000-0002-0927-680X
MacMillan, David W. C.	0000-0003-3352-4532

Additional Information:

© 2016 American Chemical Society. Received: December 19, 2015. Publication Date (Web): February 5, 2016. J. Am. Chem. Soc., Article ASAP. 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. Z.Z. and H.C. contributed equally to this work. The authors declare no competing financial interest.

Funders:

Funding Agency	Grant Number
NIH	R01 GM093213
NIH	R01 GM062871
Shanghai Institute of Organic Chemistry (SIOC)	UNSPECIFIED
Merck	UNSPECIFIED
Amgen	UNSPECIFIED

Issue or Number:

PubMed Central ID:

PMC4862596

DOI:

10.1021/jacs.5b13211

Record Number:

CaltechAUTHORS:20160216-091421574

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20160216-091421574

Official Citation:

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, and David W. C. MacMillan Journal of the American Chemical Society 2016 138 (6), 1832-1835 DOI: 10.1021/jacs.5b13211

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ID Code:

64492

Collection:

CaltechAUTHORS

Deposited By:

Ruth Sustaita

Deposited On:

17 Feb 2016 15:49

Last Modified:

10 May 2022 19:40

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