Diactivated cyclopropanes containing two geminal electron withdrawing
groups, commonly called as ‘Doubly Activated Cyclopropanes’ are useful synthons for
the synthesis of many interesting natural products and functionalized molecules. These
geminal electron withdrawing groups (EWG’s) facilitate the regioselective ring opening of
cyclopropanes by polarizing the C-C bond adjacent to it. This polarization also allows
them to undergo 1,3 dipolar cycloaddition reactions when substituted with a suitable electron
donor substituent at the adjacent carbon (donor-acceptor cyclopropanes) in the presence
of suitable dipolarophiles. In this review, we discuss the recent advances in the
chemistry of doubly activated cyclopropanes: their synthesis, reactions and applications in
total synthesis.