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1.1.7.3 Ylide-Mediated Cyclopropanation Reactions

DOI: 10.1055/sos-SD-212-00164

Belderrain, T. R.; Nicasio, M. C.Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (20141272.

The conjugate addition of an ylide to an electrophilic alkene gives an enolate intermediate from which elimination of the heteroatom-containing moiety triggers a cyclization process, rendering a cyclopropane ring. This transformation is classified as a Michael-initiated ring closure (MIRC) type reaction (Scheme 15).[‌1‌,‌12‌,‌15‌,‌90‌‌94‌] The ylide cyclopropanations of acyclic alkenes are nonstereospecific, and both E- and Z-alkenes usually produce the trans-cyclopropane due to fast rotation around the C—C bond.

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References