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5‐Hydroxy‐isoxazolidine: A New Synthetic Approach to a Privileged Heterocycle for Organic Synthesis
Author(s) -
Presenti Piero,
Moiola Mattia,
Quadrelli Paolo
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001337
Subject(s) - steric effects , adduct , markovnikov's rule , chemistry , combinatorial chemistry , organic synthesis , organic chemistry , regioselectivity , catalysis
A modified pathway towards 5‐hydroxy‐isoxazolidines has been preliminarily investigated by taking advantage of the anti‐Markovnikov route in ene reactions of sterically encumbered nitrosocarbonyl intermediates in the presence of allylsilylethers. Fluoride‐mediated deprotection/cyclization of the ene adducts afforded the desired heterocycles in quantitative yields and the methodology is adaptable to a one‐pot procedure.