5-endo-dig Cyclization of O-Propargyl Mandelic Acid Amides towards 2,5-Dihydrofurans

Lilia Ben Gaied; Nicolas Fincias; Julian Garrec; Laurent El Kaïm

doi:10.1002/ejoc.201901397

5-endo-dig Cyclization of O-Propargyl Mandelic Acid Amides towards 2,5-Dihydrofurans

Lilia Ben Gaied
, Nicolas Fincias
, Julian Garrec
, Laurent El Kaïm

University of Carthage, Institut Préparatoire aux Études Scientifiques et Techniques
Centre national de la recherche scientifique

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

Abstract

5-endo-dig cyclization of O-propargyloxyamides, obtained through a Passerini reaction mediated by boric acid and subsequent propargylation, affords 2,5-dihydrofurans in the presence of tert-butylate. The mechanism of the reaction was studied by using DFT calculations and the results were compared with the behavior of analogous N-propargylamide derivatives.

Original language	English
Pages (from-to)	7656-7665
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	47
DOIs	https://doi.org/10.1002/ejoc.201901397
Publication status	Published - 19 Dec 2019

Keywords

5-endo dig cyclization
Alkynes
DFT modelling
Dihydrofuran
Passerini adducts

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10.1002/ejoc.201901397

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@article{783a6ebe19764337853255708b3fb8e3,

title = "5-endo-dig Cyclization of O-Propargyl Mandelic Acid Amides towards 2,5-Dihydrofurans",

abstract = "5-endo-dig cyclization of O-propargyloxyamides, obtained through a Passerini reaction mediated by boric acid and subsequent propargylation, affords 2,5-dihydrofurans in the presence of tert-butylate. The mechanism of the reaction was studied by using DFT calculations and the results were compared with the behavior of analogous N-propargylamide derivatives.",

keywords = "5-endo dig cyclization, Alkynes, DFT modelling, Dihydrofuran, Passerini adducts",

author = "Gaied, \{Lilia Ben\} and Nicolas Fincias and Julian Garrec and Ka{\"i}m, \{Laurent El\}",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = dec,

day = "19",

doi = "10.1002/ejoc.201901397",

language = "English",

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journal = "European Journal of Organic Chemistry",

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T1 - 5-endo-dig Cyclization of O-Propargyl Mandelic Acid Amides towards 2,5-Dihydrofurans

AU - Gaied, Lilia Ben

AU - Fincias, Nicolas

AU - Garrec, Julian

AU - Kaïm, Laurent El

PY - 2019/12/19

Y1 - 2019/12/19

N2 - 5-endo-dig cyclization of O-propargyloxyamides, obtained through a Passerini reaction mediated by boric acid and subsequent propargylation, affords 2,5-dihydrofurans in the presence of tert-butylate. The mechanism of the reaction was studied by using DFT calculations and the results were compared with the behavior of analogous N-propargylamide derivatives.

AB - 5-endo-dig cyclization of O-propargyloxyamides, obtained through a Passerini reaction mediated by boric acid and subsequent propargylation, affords 2,5-dihydrofurans in the presence of tert-butylate. The mechanism of the reaction was studied by using DFT calculations and the results were compared with the behavior of analogous N-propargylamide derivatives.

KW - 5-endo dig cyclization

KW - Alkynes

KW - DFT modelling

KW - Dihydrofuran

KW - Passerini adducts

U2 - 10.1002/ejoc.201901397

DO - 10.1002/ejoc.201901397

M3 - Article

AN - SCOPUS:85076218034

SN - 1434-193X

VL - 2019

SP - 7656

EP - 7665

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 47

ER -

5-endo-dig Cyclization of O-Propargyl Mandelic Acid Amides towards 2,5-Dihydrofurans

Abstract

Keywords

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