Substituted diazoalkanes react smoothly, in the presence of catalytic amounts of Pd(OAc)(2), with a range of vinyl- and dienylboronates, affording in good to excellent yields, the corresponding trisubstituted cyclopropanes. The reaction is remarkably regio-, chemo-, and diastereoselective. The synthetic utility of this novel protocol is illustrated by the efficient assembly of the middle fragment of ambruticin.
Marko, I., Kumamoto, T., & Giard, T. (2002). Remarkable stereocontrol in the palladium-catalysed cyclopropanation of vinyl- and dienylboronates by substituted diazoalkanes. Advanced Synthesis & Catalysis, 344(10), 1063-1067. https://doi.org/10.1002/1615-4169(200212)344:10<1063::AID-ADSC1063>3.0.CO;2-L (Original work published 2002)