Nickel-catalyzed divergent sulfonations of propargylic carbonate

Chiral sodium sulfinates serve as crucial synthetic intermediates utilized for rapidly producing a variety of enantioenriched sulfone derivatives that are pervasive in the fields of pharmaceutical chemistry and chemical synthesis. Here we present a practical and highly effective method for the nickel-catalyzed asymmetric sulfonation of propargylic carbonates for the production of essential synthetic building blocks. Notably, sodium 1-methyl 3-sulfinopropanoate (SMOPS), a commercially available sulfonylation reagent, has potential for in situ unmasking and functionalization in the formation of enantioenriched sulfinate salts for diverse product diversification. With operational simplicity and remarkable tolerance toward diverse functional groups, this methodology provides an extensive collection of biologically relevant propargylated, allenylated, and 1,3-dienylated sulfones, with excellent yields and regio- and stereoselectivities.