title: Carbon dioxide as a protecting group: highly efficient and selective catalytic access to cyclic cis-diol scaffolds.
abstract: The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using aminotriphenolate-based metal catalysts 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.
authors.affiliation: Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es.
authors.forename: Victor
authors.initials: V
authors.lastname: Laserna
authors.forename: Giulia
authors.initials: G
authors.lastname: Fiorani
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Whiteoak
authors.forename: Eddy
authors.initials: E
authors.lastname: Martin
authors.forename: Eduardo
authors.initials: E
authors.lastname: Escudero-Adán
authors.forename: Arjan W
authors.initials: AW
authors.lastname: Kleij
keywords: aluminum; carbonates; epoxides; homogeneous catalysis; syn diols