Catalyst-Controlled Selective Alkylation/Cyclopropanation of Indoles with Vinyl Diazoesters

• DOI: 10.1021/acs.orglett.9b03323
• Publication Date: 2019-10-09T14:48:08Z
• Authors: Zhen Wang; Guangyang Xu; Shengbiao Tang; Ying Shao; Jiangtao Sun
• Keywords: 01 natural sciences; 0104 chemical sciences

A catalyst-controlled selective functionalization of indoles with vinyl diazoacetates has been developed. The use of gold catalysts exclusively leads to C3-alkylation products, whereas the highly diastereoselective cyclopropanation reaction is dominant for silver catalysis. Importantly, the gold and silver vinylcarbenes exhibit highly carbenic rather than vinylogous reactivity in these transformations.