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Diazaphospholene Precatalysts for Imine and Conjugate Reductions
Author(s) -
Adams Matt R.,
Tien ChiehHung,
Huchenski Blake S. N.,
Ferguson Michael J.,
Speed Alexander W. H.
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.201611570
Subject(s) - conjugate , imine , chemistry , mathematics , organic chemistry , catalysis , mathematical analysis
The first examples of 1,3,2‐diazaphospholene‐catalyzed imine reduction and conjugate reduction reactions are reported. This approach employs readily synthesized alkoxydiazaphospholene precatalysts that can be handled in open air. Reduction of substrates containing Lewis basic functionality, isolated unsaturation, and protic functional groups was accomplished. The synthetic utility of this approach is demonstrated by the synthesis of the important antiparkinson medicine rasagiline and the natural product zingerone.