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Brønsted Acid Catalyzed Highly Diastereoselective Michael‐Type Addition of Azlactones to Enones
Author(s) -
Ávila Eloah P.,
de Mello Amanda C.,
Diniz Renata,
Amarante Giovanni W.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300076
Subject(s) - stereocenter , chemistry , michael reaction , adduct , desymmetrization , brønsted–lowry acid–base theory , organocatalysis , addition reaction , acetone , catalysis , stereochemistry , organic chemistry , enantioselective synthesis
A highly regio‐ and diastereoselective 1,4‐addition of azlactones to enones catalyzed by a Brønsted acid is described. The Michael adducts were prepared in moderate to good yields and with complete control of the relative stereochemistry. In addition, two consecutive stereogenic centers were created, one of which was a quaternary stereocenter. The method was successfully extended to the first highly diastereoselective desymmetrization of dibenzylidene acetone.