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Palladium-Catalyzed Diastereoselective Formal [5 + 3] Cycloaddition for the Construction of Spirooxindoles Fused with an Eight-Membered Ring

Author:
Niu, Ben, Wu, Xiao-Yun, Wei, Yin, Shi, Min
Source:
Organic letters 2019 v.21 no.12 pp. 4859-4863
ISSN:
1523-7052
Subject:
Bronsted acids, carbonates, catalytic activity, cycloaddition reactions, diastereomers, diastereoselectivity, imines, ligands, oxidation, palladium, phosphine
Abstract:
A Pd-catalyzed formal [5 + 3] intermolecular cycloaddition reaction of isatin-derived α-(trifluoromethyl)imines with aryl substituted vinylethylene carbonates (VECs) has been reported, affording trifluoromethyl-group-containing spirooxindoles fused with an eight-membered ring as a single diastereoisomer in good yields in the presence of a Brønsted acid in a one-pot manner under mild conditions. The asymmetric version of this reaction has been also realized using a chiral phosphine ligand along with the further transformation of the obtained product to give a spirooxindolo pyrrolidine derivative upon oxidation.
Agid:
6478234