1‐Hydrosilatrane: A Locomotive for Efficient Ketone Reductions | Zendy

Varjosaari Sami E. | Zendy; Skrypai Vladislav | Zendy; Suating Paolo | Zendy; Hurley Joseph J. M. | Zendy; Gilbert Thomas M. | Zendy; Adler Marc J. | Zendy

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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.

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