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Synthesis of Ethyl 5‐Hydroxyisoxazolidine‐4‐carboxylates via Michael Addition/Intramolecular Hemiketalisation
Author(s) -
Benfatti Fides,
Bottoni Andrea,
Cardillo Giuliana,
Gentilucci Luca,
Monari Magda,
Mosconi Elisa,
Stenta Marco,
Tolomelli Alessandra
Publication year - 2008
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.200800719
Subject(s) - chemistry , intramolecular force , hydroxylamine , trimethylsilyl , yield (engineering) , michael reaction , stereochemistry , medicinal chemistry , organic chemistry , computational chemistry , catalysis , materials science , metallurgy
The 1,4‐addition of N , O ‐bis(trimethylsilyl)hydroxylamine to alkylideneacetoacetates gave, in high yield, new 5‐hydroxyisoxazolidine‐4‐carboxylates. The results of the accurate computational investigation on the mechanism at the DFT level are in complete agreement with the experimental evidence and the crystallographic data. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)