Carbon Dioxide as a protecting group : highly efficient and selective catalytic access to Cycliccis-Diol Scaffolds

LASERNA, Victor, FIORANI, Giulia, WHITEOAK, Christopher, MARTIN, Eddy, ESCUDERO-ADÁN, Eduardo and KLEIJ, Arjan W. (2014). Carbon Dioxide as a protecting group : highly efficient and selective catalytic access to Cycliccis-Diol Scaffolds. Angewandte Chemie International Edition, 53 (39), 10416-10419.

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.20...
Link to published version:: 10.1002/anie.201406645

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.

Item Type: Article
Identification Number: 10.1002/anie.201406645
Depositing User: Christopher Whiteoak
Date Deposited: 05 Apr 2016 14:41
Last Modified: 05 Apr 2016 14:41
URI: http://shura.shu.ac.uk/id/eprint/11774

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