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Synthesis of Tetrahydropyridazines by a Metal–Carbene‐Directed Enantioselective Vinylogous NH Insertion/Lewis Acid‐Catalyzed Diastereoselective Mannich Addition
Author(s) -
Xu Xinfang,
Zavalij Peter Y.,
Doyle Michael P.
Publication year - 2012
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.201203962
Subject(s) - lewis acids and bases , carbene , enantioselective synthesis , catalysis , chemistry , diazo , mannich reaction , yield (engineering) , insertion reaction , metal , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry , materials science , metallurgy
A versatile cascade of reactions, triggered by Rh II ‐catalyzed diazo decomposition followed by a vinylogous NH insertion/Lewis acid catalyzed Mannich addition, that produces highly substituted 1,2,3,6‐tetrahydropyridazines in up to 97 % ee with high yield and diastereocontrol has been developed.