A straightforward synthesis of α-furfuryl amide via Lewis acid-mediated allylic substitution

Xue Sun; Toshitsugu Kai; Hiroaki Takayanagi; Kimio Furuhata

doi:10.1055/s-1999-2866

A straightforward synthesis of α-furfuryl amide via Lewis acid-mediated allylic substitution

Xue Sun
, Toshitsugu Kai
, Hiroaki Takayanagi
, Kimio Furuhata

Chemistry

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

Abstract

α-(Methoxycarbonyl)furfuryl amide was prepared by Lewis acid catalyzed allylic substitution reaction of the corresponding α- (methoxycarbonyl)furfuryl carbinol acetate with various nitriles as nucleophiles, and the so-formed amides were subjected to oxidative cleavage of the furan ring to afford N-protected polyhydroxyamino acids.

Original language	English
Pages (from-to)	1399-1400
Number of pages	2
Journal	Synlett
Issue number	9
DOIs	https://doi.org/10.1055/s-1999-2866
State	Published - Jan 1 1999

Keywords

Allylic substitution
Lewis acid
Nitrile
Synthesis
α-furfuryl amide

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abstract = "α-(Methoxycarbonyl)furfuryl amide was prepared by Lewis acid catalyzed allylic substitution reaction of the corresponding α- (methoxycarbonyl)furfuryl carbinol acetate with various nitriles as nucleophiles, and the so-formed amides were subjected to oxidative cleavage of the furan ring to afford N-protected polyhydroxyamino acids.",

keywords = "Allylic substitution, Lewis acid, Nitrile, Synthesis, α-furfuryl amide",

author = "Xue Sun and Toshitsugu Kai and Hiroaki Takayanagi and Kimio Furuhata",

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AU - Sun, Xue

AU - Kai, Toshitsugu

AU - Takayanagi, Hiroaki

AU - Furuhata, Kimio

PY - 1999/1/1

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N2 - α-(Methoxycarbonyl)furfuryl amide was prepared by Lewis acid catalyzed allylic substitution reaction of the corresponding α- (methoxycarbonyl)furfuryl carbinol acetate with various nitriles as nucleophiles, and the so-formed amides were subjected to oxidative cleavage of the furan ring to afford N-protected polyhydroxyamino acids.

AB - α-(Methoxycarbonyl)furfuryl amide was prepared by Lewis acid catalyzed allylic substitution reaction of the corresponding α- (methoxycarbonyl)furfuryl carbinol acetate with various nitriles as nucleophiles, and the so-formed amides were subjected to oxidative cleavage of the furan ring to afford N-protected polyhydroxyamino acids.

KW - Allylic substitution

KW - Lewis acid

KW - Nitrile

KW - Synthesis

KW - α-furfuryl amide

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ER -

A straightforward synthesis of α-furfuryl amide via Lewis acid-mediated allylic substitution

Abstract

Keywords

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