Open AccessStereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen’s Amine
Author(s) -
Faben A. Cruz,
Vy M. Dong
Publication year - 2017
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.6b10680
Subject(s) - chemistry , stereocenter , regioselectivity , vicinal , enantioselective synthesis , amine gas treating , catalysis , quaternary carbon , combinatorial chemistry , stereoisomerism , organocatalysis , stereochemistry , organic chemistry
We report an enantioselective coupling between α-branched aldehydes and alkynes to generate vicinal quaternary and tertiary carbon stereocenters. The choice of Rh and organocatalyst combination allows for access to all possible stereoisomers with high enantio-, diastereo-, and regioselectivity. Our study highlights the power of catalysis to activate two common functional groups and provide access to divergent stereoisomers and constitutional structures.