3 years ago

Enantioselective Decarboxylative α-Alkynylation of β-Ketocarbonyls via a Catalytic α-Imino Radical Intermediate

Enantioselective Decarboxylative α-Alkynylation of β-Ketocarbonyls via a Catalytic α-Imino Radical Intermediate
Sanzhong Luo, Long Zhang, Dehong Wang
A distinctive aminocatalysis via α-imino radical is reported on the basis of SET oxidation of a secondary enamine. The combination of chiral primary amine catalysis and visible-light photoredox catalysis enables the enantioselective decarboxylative coupling of propiolic acid and β-ketocarbonyls to afford alkynylation adducts with high enantioselectivity. Mechanism studies indicate the reaction proceeds via an α-imino radical addition.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02386

DOI: 10.1021/acs.orglett.7b02386

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