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5‐ endo‐dig Cyclization of O‐Propargyl Mandelic Acid Amides towards 2,5‐Dihydrofurans
Author(s) -
Gaied Lilia Ben,
Fincias Nicolas,
Garrec Julian,
Kaïm Laurent El
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901397
Subject(s) - chemistry , dig , propargyl , boric acid , mandelic acid , medicinal chemistry , reaction mechanism , mechanism (biology) , stereochemistry , organic chemistry , catalysis , computer security , computer science , philosophy , epistemology
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.