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Stereospecific Synthesis of Alkylidenecyclopropanes via Sequential Cyclopropene Carbomagnesation/1,3-Carbon Shift

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journal contribution
posted on 04.06.2010, 00:00 authored by Xiaocong Xie, Zhe Yang, Joseph M. Fox
Alkylidenecyclopropanes can be synthesized from enantiomerically enriched cyclopropene derivatives with >99% stereotransfer and good to excellent yield. The protocol comprises the stereoselective reaction of Grignard reagents with 1-alkoxymethyl-3-hydroxymethylcyclopropenes and a stereospecific [1,3] carbon shift reaction.