Synthesis of 5‐Phosphonoisoxazol­ine N‐Oxides by Selective O‐Alkylation of Nitronate Anions. Issue 2 (20th November 2015)

• Record Type: Journal Article
• Authors: Perez, Vincent; Rabasso, Nicolas; Fadel, Antoine
• Is Part Of: European journal of organic chemistry. Issue 2 (2016)
• Page Start: 320
• Page End: 324
• Publication Date: 2015-11-20
• Subjects: Heterocycles -- Cyclization -- Phosphorus -- Small ring systems -- Alkylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501243
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : 5‐Phosphonoisoxazoline N ‐oxides are prepared in good to excellent yields by selective O ‐alkylation of nitronate anions with (α‐tosyloxyvinyl)phosphonates. A comprehensive study is undertaken to limit the competitive formation of the (β‐nitrocyclopropyl)phosphonate resulting from C ‐alkylation of the ambident nitronate anions. Ts = para ‐tolylsulfonyl, DBU = 1, 8‐diazabicyclo[5.4.0]undec‐7‐ene.