Phosphane-catalyzed [4+1] annulation between nitroalkenes and Morita-Baylis-Hillman carbonates: facile synthesis of isoxazoline N-oxides by phosphorus ylides.
A phosphane-catalyzed [4+1] annulation between nitroalkenes and Morita-Baylis-Hillman carbonates has been realized; this provides facile and diastereoselective access to polysubstituted isoxazoline N-oxides in moderate to excellent yields. In the annulation, an in situ formed allylic phosphorus ylide presumably serves as a pivotal active intermediate. This reaction accordingly represents the first example of phosphorus ylide initiated [4+1] cyclization of nitroalkenes to give isoxazoline N-oxides.
College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024 (P.R. China), Fax: (+86) 351-6010121; The State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) and Department of Chemistry, Nankai University, Tianjin 300071 (P.R. China), Fax: (+86) 22-23501520.
Rong
R
Zhou
Chong
C
Duan
Changjiang
C
Yang
Zhengjie
Z
He
D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D007536:Isomerism; D007555:Isoxazoles / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D010758:Phosphorus / Q000737:chemistry*
D002254:Carbonates; D007555:Isoxazoles; D010087:Oxides; D010720:Phosphines; D010758:Phosphorus; C044646:phosphine
annulation; isoxazolines; phosphanes; reaction mechanisms; ylides