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A third mode of reactivity for allylsilanes in their reactions with α,β-unsaturated carbonyl compounds has been found in addition to the Sakurai reaction and the [3 + 2] cycloaddition. Silylmethyl-cyclobutanes are formed regioselectively via a siliranium ion intermediate (1). The reaction with methyl propynoate provides bicyclo[2.2.0]hexanes in a one-pot conversion.