5‐Hydroxy‐isoxazolidine: A New Synthetic Approach to a Privileged Heterocycle for Organic Synthesis | Zendy

Presenti Piero | Zendy; Moiola Mattia | Zendy; Quadrelli Paolo | Zendy

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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.

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