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Ultrafast Iron‐Catalyzed Reduction of Functionalized Ketones: Highly Enantioselective Synthesis of Halohydrines, Oxaheterocycles, and Aminoalcohols
Author(s) -
Blasius Clemens K.,
Vasilenko Vladislav,
Gade Lutz H.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806196
Subject(s) - enantioselective synthesis , catalysis , chemistry , hydroboration , alkyl , metal , combinatorial chemistry , organic chemistry
A molecularly defined chiral boxmi iron alkyl complex catalyzes the hydroboration of various functionalized ketones and provides the corresponding chiral halohydrines, oxaheterocycles (oxiranes, oxetanes, tetrahydrofurans, and dioxanes) and amino alcohols with excellent enantioselectivities (up to >99 % ee ) and conversion efficiencies at low catalyst loadings (as low as 0.5 mol %). Turnover frequencies of greater than 40000 h −1 at −30 °C highlight the activity of this earth‐abundant metal catalyst which tolerates a large number of functional groups.