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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.