Diastereoselective synthesis of N-aryl tetrahydroquinolines and N-aryl indolines by the tandem reaction of arynes.

A tandem reaction of arynes with α- or β-amino ketones has been revealed. Arynes react with β-amino ketones through a cascade insertion-cyclization process to afford N-aryl tetrahydroquinolines in good yield with excellent anti-selectivity. Meanwhile, the coupling of arynes with α-amino ketones produces multisubstituted indolines in high yield with syn-selectivity.

NHCs catalyzed hydrophosphonylation of α-ketoesters and α-trifluoromethyl ketones.

N-Heterocyclic carbenes catalyzed hydrophosphonylation reaction of α-ketoesters and α-trifluoromethyl ketones was developed. Under the catalysis of 10 mol% IPr, α-ketoesters or α-trifluoromethyl ketones reacted with dialkyl phosphites to provide quaternary α-hydroxyphosphonates in good to excellent yield.