Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis‐Diol Scaffolds1. Issue 39 (11th August 2014)

• Record Type: Journal Article
• Authors: Laserna, Victor; Fiorani, Giulia; Whiteoak, Christopher J.; Martin, Eddy; Escudero‐Adán, Eduardo; Kleij, Arjan W.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 39(2014)
• Page Start: 10416
• Page End: 10419
• Publication Date: 2014-08-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201406645
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The efficient and highly selective formation of a wide range of (hetero)cyclic <italic>cis</italic>‐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 <italic>cis</italic>‐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.</p> </abstract>