Synthesis of 5‐Phosphonoisoxazoline  N ‐Oxides by Selective  O ‐Alkylation of Nitronate Anions | Zendy

Perez Vincent | Zendy; Rabasso Nicolas | Zendy; Fadel Antoine | Zendy

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Synthesis of 5‐Phosphonoisoxazoline N ‐Oxides by Selective O ‐Alkylation of Nitronate Anions

Author(s) -

Perez Vincent,

Rabasso Nicolas,

Fadel Antoine

Publication year - 2016

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.201501243

Subject(s) - nitronate , chemistry , alkylation , phosphonate , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl , nitro

A series of 5‐phosphonoisoxazoline N ‐oxides were prepared in good to excellent yields by selective O ‐alkylation of nitronate anions with (α‐tosyloxyvinyl)phosphonates. A comprehensive study was undertaken to limit the competitive formation of the (β‐nitrocyclopropyl)phosphonate resulting from C ‐alkylation of the ambident nitronate anions. The 5‐phosphonoisoxazoline N ‐oxides thus formed were reduced to the corresponding 5‐phosphonoisoxazolines.

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