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1‐Hydrosilatrane: A Locomotive for Efficient Ketone Reductions
Author(s) -
Varjosaari Sami E.,
Skrypai Vladislav,
Suating Paolo,
Hurley Joseph J. M.,
Gilbert Thomas M.,
Adler Marc J.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601256
Subject(s) - chemistry , ketone , enantioselective synthesis , alkoxide , activator (genetics) , menthone , organic chemistry , lewis acids and bases , combinatorial chemistry , catalysis , menthol , biochemistry , gene
An efficient method for the reduction of ketones with 1‐hydrosilatrane is described. In the presence of a Lewis base activator, the resulting secondary alcohols are rapidly formed in good to excellent yields (20 examples, 71–99 % yields). The relative bulkiness of 1‐hydrosilatrane also enables the diastereoselective reduction of (–)‐menthone to (+)‐neomenthol, and the use of a chiral alkoxide activator can lead to the enantioselective reduction of prochiral ketones.