Highly regio- and stereoselective synthesis of cyclic carbonates from biomass-derived polyols via organocatalytic cascade reaction

Abstract

The cascade reaction of CO₂, vicinal diols, and propargylic alcohol, was firstly achieved by dual Lewis base (LB) organocatalytic systems involving LB–CO₂ adducts and commercially available organic amines. This methodology could overcome the chemical inertness of CO₂, providing an alternative route to various functionalized five-membered cyclic carbonates in moderate to high yields under mild reaction conditions (25 °C, 1.0 atm of CO₂). More importantly, this method could also be applied for facile and efficient synthesis of chiral polycyclic carbonates from biomass-derived polyols with complete configuration retention of chiral centers. This study provides an environment-friendly, scalable and cost effective protocol to construct value-added cyclic carbonates with multi-functional groups and chiral centers.