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


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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/71394

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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