Palladium‐Catalyzed Asymmetric Decarboxylative Cycloaddition of Vinylethylene Carbonates with Michael Acceptors: Construction of Vicinal Quaternary Stereocenters | Zendy

Khan Ajmal | Zendy; Yang Lei | Zendy; Xu Jing | Zendy; Jin Long Yi | Zendy; Zhang Yong Jian | Zendy

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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.

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