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Palladium‐Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Michael Acceptors: Construction of Vicinal Quaternary Stereocenters
Author(s) -
Khan Ajmal,
Yang Lei,
Xu Jing,
Jin Long Yi,
Zhang Yong Jian
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407013
Subject(s) - stereocenter , vicinal , palladium , chemistry , enantioselective synthesis , cycloaddition , phosphoramidite , catalysis , michael reaction , organic chemistry , combinatorial chemistry , dna , biochemistry , oligonucleotide
An efficient method for the diastereo‐ and enantioselective construction of vicinal all‐carbon quaternary stereocenters through palladium‐catalyzed decarboxylative cycloaddition of vinylethylene carbonates with activated Michael acceptors was developed. By using a palladium complex generated in situ from [Pd 2 (dab) 3 ]⋅CHCl 3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process provides multifunctionalized tetrahydrofurans bearing vicinal all‐carbon quaternary stereocenters in high yields with a high level of absolute and relative stereocontrol.