Catalyst-Free Stereocontrolled Formal [3 + 2]-Cycloaddition of CO2 for the Synthesis of Enantiopure Spiro[indoline-3,5'-oxazolidine]-2,2'-diones under Aqueous and Ambient Conditions.

A highly efficient regio- and stereoselective spontaneous formal [3 + 2]-cycloaddition of CO2 in aqueous medium is developed for the one-pot synthesis of spiro[indoline-3,5'-oxazolidine]-2,2'-diones with excellent enantiopuirity (ee up to 99%) under catalyst-free and ambient conditions. The detailed study reveals NH-spiroaziridine- and 3-(aminomethyl)-3-chloro-oxindoles, two in situ generated reactive intermediate compounds for the spontaneous cycloaddition with CO2, and the latter is responsible for the stereoselectivity. An unprecedented mechanism of desulfinylation is also disclosed herewith.