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Calcium-Catalyzed Cyclopropanation

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Abstract

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No transition metal needed: A calcium-catalyzed cycloisomerization yields highly substituted cyclopropanes with excellent diastereoselectivity (see scheme; Nu=nucleophile, Ts=p-toluenesulfonyl). The reaction is based on the equilibrium of a homoallenyl cation with its cyclopropane congener, which is known for gold-catalyzed reactions. According to mechanistic analysis the carbocation cascade is concerted asynchronous, and hence biomimetic.

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