An efficient cyclopropanation of olefins with Zn(CH2I)2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates, can be cyclopropanated in 71-99% yield.
An efficient acid-catalyzed sulfetherification of various unsaturated alcohols with sulfenamides to form tetrahydrofurans and tetrahydropyrans regioselectively is described. Mechanistic studies have shown that the tetrahydrofurans can stereoselectively rearrange to the corresponding tetrahydropyrans.
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