Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis-Diol Scaffolds

摘要

The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using aminolriphe-nolate-based metal catalysis is reported. The key intermediates are cyclic carbonates, which are obtained in high yield and with high levels of diastereo- and chemoselectivity from the parent oxirane precursors and carbon dioxide. Deprotection of the carbonate structures affords synthetically useful cis-diol scaffolds with different ring sizes that incorporate various functional groups. This atom-efficient method allows the simple construction of diol synthons using inexpensive and accessible precursors and green metal catalysts and. showcases the use of CO2 as a temporary protecting group.