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Enantioselective Organocatalytic Intramolecular Aza‐Diels–Alder Reaction
Author(s) -
Jarrige Lucie,
Blanchard Florent,
Masson Géraldine
Publication year - 2017
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.201705746
Subject(s) - enantioselective synthesis , intramolecular force , diels–alder reaction , catalysis , chemistry , organic chemistry , combinatorial chemistry , stereochemistry
A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2‐azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo‐ and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.