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Asymmetric Brønsted Acid Catalysis Enabling Hydroaminations of Dienes and Allenes
Author(s) -
Dion Isabelle,
Beauchemin André M.
Publication year - 2011
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.201102408
Subject(s) - hydroamination , intramolecular force , brønsted–lowry acid–base theory , catalysis , chemistry , reactivity (psychology) , sequence (biology) , organic chemistry , combinatorial chemistry , medicinal chemistry , alternative medicine , pathology , medicine , biochemistry
Acid treatment : Toste et al. recently unveiled a new pathway for asymmetric Brønsted acid catalysis of reactions involving dienes or allenes, and achieved highly efficient intramolecular hydroamination and hydroarylation reactions (see scheme). The PS bond proved necessary for reactivity, and dithiophosphoric acids emerged as efficient catalysts. The association/displacement sequence led to chiral pyrrolidines and isoxazolidines in excellent yields and ee values.