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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. http://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:
URLURL TypeDescription
http://dx.doi.org/10.1021/jacs.5b13211DOIArticle
http://pubs.acs.org/doi/abs/10.1021/jacs.5b13211PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jacs.5b13211PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4862596/PubMed CentralArticle
ORCID:
AuthorORCID
Choi, Junwon0000-0001-6004-5524
Fu, Gregory C.0000-0002-0927-680X
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 AgencyGrant Number
NIHR01 GM093213
NIHR01 GM062871
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
PubMed Central ID:PMC4862596
Record Number:CaltechAUTHORS:20160216-091421574
Persistent URL:http://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
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64492
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:17 Feb 2016 15:49
Last Modified:13 Apr 2017 23:25

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