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Enantioselective Addition Reaction of Azlactones with Styrene Derivatives Catalyzed by Strong Chiral Brønsted Acids
Author(s) -
Kikuchi Jun,
Terada Masahiro
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903111
Subject(s) - stereocenter , enantioselective synthesis , brønsted–lowry acid–base theory , catalysis , chemistry , nucleophile , intermolecular force , vicinal , styrene , organic chemistry , asymmetric carbon , combinatorial chemistry , molecule , alkyl , copolymer , polymer
An enantioselective intermolecular addition reaction of azlactones, as carbon nucleophiles, with styrene derivatives, as simple olefins, was demonstrated using a newly developed chiral Brønsted acid catalyst, namely, F 10 BINOL‐derived N ‐triflyl phosphoramide. Addition products having vicinal tetrasubstituted carbon centers, one of which is an all‐carbon quaternary stereogenic center, were formed in good yields with moderate to high stereoselectivities. Extremely high acidity of the new chiral Brønsted acid was confirmed by its calculated p K a value based on DFT studies and is the key to accomplishing not only high catalytic activity but also efficient stereocontrol in the intermolecular addition.