Synthesis of Tetrahydropyridazines by a Metal–Carbene‐Directed Enantioselective Vinylogous NH Insertion/Lewis Acid‐Catalyzed Diastereoselective Mannich Addition | Zendy

Xu Xinfang | Zendy; Zavalij Peter Y. | Zendy; Doyle Michael P. | Zendy

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Synthesis of Tetrahydropyridazines by a Metal–Carbene‐Directed Enantioselective Vinylogous NH 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.

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