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Due to high ring strain energies, cyclopropanols and cyclobutanols have a strong tendency of breaking the endocyclic C–C bonds to participate in versatile organic transformations. With an inherent three-dimensional structure, cyclopropanols and cyclobutanols have the advantage of synthesizing linear or cyclic molecules with stereogenic centers via ring-opening asymmetric synthesis. There are three strategies for the ring-opening of cyclopropanols and cyclobutanols usually involved in asymmetric synthesis: 1) β-carbon elimination of metal alkoxide; 2) radical ring-opening; 3) ring-opening via semipinacol rearrangement. The present review has highlighted the progress developed in the last five years.