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Recent Advances in the Chemistry of Doubly Activated Cyclopropanes: Synthesis and Reactivity

[ Vol. 23 , Issue. 3 ]

Author(s):

Purushothaman Gopinath* and Srinivasan Chandrasekaran*   Pages 276 - 312 ( 37 )

Abstract:


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.

Keywords:

Cyclopropanes, ring-opening, cycloaddition, diazo compounds, iodonium ylides, heterocycles, carbocycles.

Affiliation:

Department of Chemistry, Indian Institute of Science Education and Research (IISER) Tirupati, Tirupati 517507, Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012

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