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

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	7656-7665
Nombre de pages	10
journal	European Journal of Organic Chemistry
Volume	2019
Numéro de publication	47
Les DOIs	https://doi.org/10.1002/ejoc.201901397
état	Publié - 19 déc. 2019

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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",

volume = "2019",

pages = "7656--7665",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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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

UR - https://www.scopus.com/pages/publications/85076218034

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

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