Cyclopropylcarbinyl cation chemistry in synthetic method development and natural product synthesis: cyclopropane formation and skeletal rearrangement

Abstract

Cyclopropylcarbinyl cations have been an important class of non-classical carbocationic intermediates. Despite their delocalized cationic character and facile interconversion with homoallyl cations, cyclopropylcarbinyl cations can be harnessed as key intermediates in many synthetically useful transformations. In this review, key applications of cyclopropylcarbinyl cation chemistry are discussed with a focus on cyclopropane formation and skeletal rearrangement in complex molecule synthesis.