Enantiospecific Synthesis of 1,3-Disubstituted Allenes from Propargylic Carbonates through a Borylation-1,2-Elimination Process

An array of enantioenriched vinyl boronates bearing an allylic carbonate moiety have been prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF affords enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination in good yields and high enantiospecificities.

Automated summary

An array of enantioenriched vinyl boronates with an allylic carbonate moiety were prepared through selective hydroboration of propargyl carbonates. Treatment of these vinyl boronates with TBAF in THF resulted in the formation of enantioenriched 1,3-disubstituted allenes through a novel 1,2-anti elimination.