Download PDF
Synfacts 2016; 12(4): 0387
DOI: 10.1055/s-0035-1561772
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Decarboxylative Coupling by Photoredox and Chiral Nickel Catalysis

Contributor(s):
Hisashi Yamamoto
,
Ramesh C. Samanta
Zuo Z, Cong H, Li W, Choi J, Fu GC, * MacMillan DW. C. * California Institute of Technology, Pasadena and Princeton University, USA
Enantioselective Decarboxylative Arylation of α-Amino Acids via the Merger of Photoredox and Nickel Catalysis.

J. Am. Chem. Soc. 2016;
138: 1832-1835
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
15 March 2016 (online)

 
 PDF Download Permissions and Reprints

Key words

asymmetric catalysis - coupling reaction - photoredox - nickel - decarboxylation

Significance

The authors present an asymmetric arylation of α-amino acids by using a dual photo­redox/chiral nickel catalysis approach. A broad array of naturally occurring α-amino acids were arylated with various aryl halides to generate high-value chiral benzylic amines in high yields and with high enantioselectivities.


#

Comment

The authors have previously reported the coupling of aryl halides with an α-carboxy sp3 carbon by dual photoredox reaction/nickel catalysis (Science 2014, 345, 437). Identification of chiral ligands compatible with a nickel catalyst under photoredox conditions permitted an asymmetric transformation. Chiral benzylamines that form the core structures of many pharmaceutically active molecules have been synthesized in optically pure form by this method.


#
#


   Permissions and Reprints