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Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ

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Title: Nucleophilic Addition of Alkanenitriles to Aldehydes via N-Silyl Ketene Imines Generated In Situ
Authors: Tanino, Keiji Browse this author →KAKEN DB
Yoshimura, Fumihiko Browse this author
Saito, Hiroki Browse this author
Abe, Taiki Browse this author
Keywords: nitriles
nitrile aldol reaction
nucleophilic addition
N-silyl ketene imines
aldehydes
Issue Date: Sep-2017
Journal Title: Synlett
Volume: 28
Issue: 14
Start Page: 1816
End Page: 1820
Publisher DOI: 10.1055/s-0036-1588424
Abstract: Upon treatment with triisopropylsilyl trifluoromethanesulfonate and 2,2,6,6-tetramethylpiperidine, alkanenitriles undergo direct addition to aldehydes under mild non-basic neutral conditions to provide triisopropylsilyl ethers of β-hydroxy nitriles in good yield. The reaction proceeds through generation of an N-silyl ketene imine intermediate in situ from the alkanenitrile followed by nucleophilic addition of the intermediate to the aldehyde.
Description: Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588424.
Type: article (author version)
URI: http://hdl.handle.net/2115/71394
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 吉村 文彦

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