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Development of Chiral Organosuperbase Catalysts Consisting of Two Different Organobase Functionalities
Author(s) -
Kondoh Azusa,
Oishi Masafumi,
Tezuka Hikaru,
Terada Masahiro
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202001419
Subject(s) - enantioselective synthesis , catalysis , brønsted–lowry acid–base theory , substrate (aquarium) , combinatorial chemistry , organocatalysis , base (topology) , chemistry , organic chemistry , nanotechnology , topology (electrical circuits) , materials science , mathematics , mathematical analysis , oceanography , combinatorics , geology
In the field of chiral Brønsted base catalysis, a new generation of chiral catalysts has been highly anticipated to overcome the intrinsic limitation of pronucleophiles that are applicable to the enantioselective reactions. Herein, we reveal conceptually new chiral Brønsted base catalysts consisting of two different organobase functionalities, one of which functions as an organosuperbase and the other as the substrate recognition site. Their prominent activity, which stems from the distinctive cooperative function by the two organobases in a single catalyst molecule, was demonstrated in the unprecedented enantioselective direct Mannich‐type reaction of α‐phenylthioacetate as a less acidic pronucleophile. The present achievement would provide a new guiding principle for the design and development of chiral Brønsted base catalysts and significantly broaden the utility of Brønsted base catalysis in asymmetric organic synthesis.