Enantioselective Aza-Ene-type Reactions of Enamides with Gold Carbenes Generated from α-Diazoesters.

Research paper by Feng F Zhao, Nan N Li, Tao T Zhang, Zhi-Yong ZY Han, Shi-Wei SW Luo, Liu-Zhu LZ Gong

Indexed on: 15 Feb '17Published on: 15 Feb '17Published in: Angewandte Chemie International Edition


Carbophilic gold carbenes generated from the decomposition of α-diazoesters show high reactivity towards enamides, leading to an unprecedented aza-ene-type reaction. The presence of 0.1 mol % of a chiral Brønsted acid co-catalyst is sufficient to give synthetically relevant γ-keto esters in excellent yields and selectivities (up to 99 % yield, 97 % ee).