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Competitive Formation of β‐Enaminones and 3‐Amino‐2(5 H )‐furanones from the Isoxazolidine System: A Combined Synthetic and Quantum Chemical Study
Author(s) -
Iannazzo Daniela,
Brunaccini Elisa,
Giofrè Salvatore V.,
Piperno Anna,
Romeo Giovanni,
Ronsisvalle Simone,
Chiacchio Maria A.,
Lanza Giuseppe,
Chiacchio Ugo
Publication year - 2010
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.201000579
Subject(s) - chemistry , quantum chemical , solvent , base (topology) , computational chemistry , fluoride , combinatorial chemistry , stereochemistry , organic chemistry , medicinal chemistry , molecule , inorganic chemistry , mathematical analysis , mathematics
Treatment of 3‐alkoxycarbonyl‐4‐acyl‐ or 3,4‐dialkoxycarbonyl‐substituted isoxazolidines with a mild base, such as tetrabutylammonium fluoride, affords β‐enaminones and/or 3‐methylamino‐2(5 H )‐furanones according to the nature of the substituents at C 4 and C 5 . Two alternative mechanisms (lactonization and retro‐aldolization) have been rationalized by DFT quantum chemical methods. Any realistic theoretical modeling requires the explicit inclusion of countercation and solvent effects.