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1‐Hydrosilatrane: A Locomotive for Efficient Ketone Reductions

2016; Wiley; Volume: 2017; Issue: 2 Linguagem: Inglês

10.1002/ejoc.201601256

1434-193X

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

Chemical Synthesis and Reactions

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.