Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes

Abstract

1,2-Disubstituted 3-hydroxymethylcyclopropene derivatives have been synthesized by reacting the dianions of 1-alkyl-3-hydroxymethylcyclopropenes with a range of electrophiles. Additionally, a complementary procedure is described for one-pot sequential alkylation/rearrangement to provide a convenient synthesis of a chiral methylenecyclopropane directly from a 1-alkyl-3-hydroxymethylcyclopropene.

Key words

cyclopropene - chirality - dianions - strained ring systems - rearrangement

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