CYCLOADDITIONS OF ALLYLSILANES .10. STEREOSELECTIVE CONSTRUCTION OF RING-SYSTEMS BY CYCLOADDITION REACTIONS OF ALLYLTRIISOPROPYLSILANE

Allyltriisopropylsilane is a useful reagent for the stereoselective co nstruction of various ring systems by Lewis acid promoted formal cyclo addition reactions. The reaction of allyltriisopropylsilane as a synth etic equivalent of a 1,3-dipole in [3+2] and [3+3] cycloadditions prov ides cyclopentanes, tetrahydrofurans, and tetrahydronaphthalenes. [2+2 ] and [2+3] Cycloadditions of allyltriisopropylsilane as a synthetic e quivalent of a 1,2-dipole provide cyclobutanes, oxetanes, azetidines, and dihydrofurans.