Synfacts 2019; 15(03): 0255
DOI: 10.1055/s-0037-1612235
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric 1,2-Dicarbofunctionalization of Alkenes with Copper/Chiral Phosphoric Acid System

Mark Lautens
Egor M. Larin
Lin JS, Li TT, Liu J.-R, Jiao G.-Y, Gu Q.-S, Cheng J.-T, Guo Y.-L, Hong X. * Liu X.-Y. * Southern University of Science and Technology, Shenzhen and Zhejiang University, Hangzhou, P. R. of China
Cu/Chiral Phosphoric Acid-Catalyzed Asymmetric Three-Component Radical-Initiated 1,2-Dicarbofunctionalization of Alkenes.

J. Am. Chem. Soc. 2019;
141: 1074-1083
Further Information

Publication History

Publication Date:
15 February 2019 (online)



Owing to their ready availability, asymmetric dicarbofunctionalization of alkenes remains an important topic in catalysis. The authors report a three-component asymmetric difunctionalization of 1,1-disubstituted alkenes with a radical initiator and heteroaryl nucleophile using copper and chiral phosphoric acid (CPA) catalyst.



The reaction proceeds through a Kharasch-type addition across the unactivated olefin, whereupon the resultant tertiary radical undergoes a SET to form a tertiary cation. The CPA’s H-bonding affects the facial selectivity of the attack of the indole moiety in an asymmetric fashion to form the products.