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Chiral 1,3,2‐Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions
Author(s) -
Miaskiewicz Solène,
Reed John H.,
Donets Pavel A.,
Oliveira Caio C.,
Cramer Nicolai
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201801300
Subject(s) - enantioselective synthesis , conjugate , catalysis , chemistry , combinatorial chemistry , stereoisomerism , stereochemistry , medicinal chemistry , organic chemistry , mathematical analysis , mathematics
Secondary 1,3,2‐diazaphospholenes have a polarized P−H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy‐1,3,2‐diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4‐reductions of α,β‐unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.