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Catalytic Enantioselective Intramolecular Aza‐Diels–Alder Reactions
Author(s) -
Min Chang,
Lin ChihTsung,
Seidel Daniel
Publication year - 2015
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.201501536
Subject(s) - intramolecular force , enantioselective synthesis , stereocenter , catalysis , diels–alder reaction , chemistry , brønsted–lowry acid–base theory , organic chemistry
A readily available chiral Brønsted acid was identified as an efficient catalyst for intramolecular Povarov reactions. Polycyclic amines containing three contiguous stereogenic centers were obtained with excellent stereocontrol in a single step from secondary anilines and aldehydes possessing a pendent dienophile. These transformations constitute the first examples of catalytic enantioselective intramolecular aza‐Diels–Alder reactions.