Anti-Selective Cyclopropanation of Non-Conjugated Alkenes with Diverse Pronucleophiles via Directed Nucleopalladation

A facile approach to densely functionalized cyclopropanes is described. The reaction proceeds under mild conditions via the directed nucleopalladation of non-conjugated alkenes with readily available pronucleophiles and gives excellent yields and good anti-selectivity using I2 and TBHP as oxidants. Pronucleophiles bearing a diverse collection electron-withdrawing groups, including–CN, –CO2R, –COR, –SO2Ph, -CONHR and –NO2, are well tolerated. Internal alkenes, which are generally challenging substrates in other cyclopropanation methods, provide excellent yields and good diastereoselectivity in this methodology, allowing for controlled access to cyclopropanes substituted at all three C-atoms.