SILYL NITRONATES, NITRILE OXIDES, AND DERIVED 2-ISOXAZOLINES IN ORGANIC SYNTHESIS. FUNCTIONALIZATION OF BUTADIENE, A NOVEL ROUTE TO FURANS AND 2-ISOXAZOLINES AS AN ALTERNATIVE TO ALDOL-TYPE CONDENSATIONS

Article abstract of DOI:10.1016/S0040-4020(01)91947-7

Mono- and di-addition of silylnitronates and nitrile oxides is a useful procedure for functionalizing butadiene leading to cyano and acyl derivatives.A novel route to 2,5-disubstituted furans is also established.The potential of the method in carbohydrate synthesis is pointed out.The route via 2-isoxazoline is shown to be a useful alternative to aldol-type reactions in organic synthesis. 15a has been studied by X-ray diffraction and shown to be meso form.