Chiral α‑Amino Acid/Palladium-Catalyzed Asymmetric Allylation of α‑Branched β‑Ketoesters with Allylic Amines: Highly Enantioselective Construction of All-Carbon Quaternary Stereocenters

A new protocol has been developed for the use of allylic amines as allylating agents in the chiral α-amino acid/palladium-catalyzed asymmetric allylation of α-branched β-ketoesters, providing highly enantioselective access to all-carbon quaternary stereocenters. Notably, the formation of a primary a...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-11, Vol.84 (22), p.14936-14942
Main Authors: Xu, Ya-Nan, Zhu, Meng-Zeng, Tian, Shi-Kai
Format: Article
Language:English
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Summary:A new protocol has been developed for the use of allylic amines as allylating agents in the chiral α-amino acid/palladium-catalyzed asymmetric allylation of α-branched β-ketoesters, providing highly enantioselective access to all-carbon quaternary stereocenters. Notably, the formation of a primary amine, a secondary amine, or ammonia as a byproduct has little influence on the enantioselectivity for the catalytic asymmetric synthesis of structurally diverse α,α-disubstituted β-ketoesters.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02282