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Synfacts 2019; 15(03): 0255
DOI: 10.1055/s-0037-1612235
DOI: 10.1055/s-0037-1612235
Metals in Synthesis
Asymmetric 1,2-Dicarbofunctionalization of Alkenes with Copper/Chiral Phosphoric Acid System
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
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)
Significance
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.
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Comment
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.
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