Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes

A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.

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Bibliographic Details
Published in:Tetrahedron letters 2012-07, Vol.53 (27), p.3527-3529
Main Authors: Kim, Joong-Gon, Mishra, Mithilesh Kumar, Jang, Doo Ok
Format: Article
Language:English
Subjects:
Aldehyde
Aldehydes
Boranes
Iodides
Ketone
Ketones
O-triphenylsilylated oxime
Oximes
Synthesis (chemistry)
Tetrahedrons
Triethyl borane
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Description
Summary:A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.05.005