ИСТИНА

In this work we present extended [3] Corey-Chaykovsky reaction as a versatile approach for synthesis of benzylcyclopropanes 2 and their analogs 3 via reaction of the excess of Corey ylide with readily available 4-hydroxyphenyl- and 1H- or 1-p-tosyl 3-indolyl-substituted alkenes 1. This reaction proceeds as double methylene transfer from Corey ylide to activated Knoevenagel adducts. Investigation of mechanism, including studies of deuterium labelled Corey ylide, allowed us to conclude that the presence of electron releasing groups in (het)aryl substituent and ability to ipso attack play a crucial role for the realization of this domino process. Oppositely, common cyclopropanes 4,5 were obtained using substrates bearing 3-nitro- or 4-TsNH groups.