C(sp(3))-H Functionalizations Promoted by the Gold Carbene Generated from Vinylidenecyclopropanes

摘要

The gold carbene generated from vinylidenecyclopropanes (VDCPs) can smoothly perform a C(sp(3))-H bond insertion reaction, stereoselectively affording the intramolecular C(sp(3))-H bond functionalized product, benzoxepine, with syn-configuration in moderate to good yields under mild conditions. The KIE investigation on this bond functionalization partially revealed that the carbene insertion step might be rate-determining. Using a chiral gold(I) catalyst, the first example on the asymmetric variant of gold carbene insertion into C(sp(3))-H bond has been disclosed, giving the desired products with excellent results.