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Palladium‐Catalyzed Asymmetric Construction of Vicinal All‐Carbon Quaternary Stereocenters and its Application to the Synthesis of Cyclotryptamine Alkaloids
Author(s) -
Trost Barry M.,
Osipov Maksim
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302805
Subject(s) - stereocenter , vicinal , tsuji–trost reaction , enantioselective synthesis , palladium , catalysis , chemistry , alkylation , stereochemistry , quaternary carbon , combinatorial chemistry , organic chemistry
A twofold Pd‐DAAA Pd‐catalyzed decarboxylative allylic alkylation (see scheme) was used to construct two vicinal all‐carbon quaternary stereocenters (marked in red) in a diastereo‐ and enantioselective fashion. The products of the Pd‐DAAA were further elaborated to complete the formal syntheses of cyclotryptamine alkaloids. The twofold Pd‐catalyzed transformation proceeds through an initial matched allylation followed by a second mismatched allylation to deliver the desired product.