Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis‐Diol Scaffolds |
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| Authors: | Victor Laserna Dr. Giulia Fiorani Dr. Christopher J. Whiteoak Dr. Eddy Martin Eduardo Escudero‐Adán Prof. Dr. Arjan W. Kleij |
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| Affiliation: | 1. Institute of Chemical Research of Catalonia (ICIQ), Av. Pa?sos Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es;2. Catalan Institute for Research and Advanced Studies (ICREA), Pg. Lluís Companys 23, 08010 Barcelona (Spain) |
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| 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. |
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| Keywords: | aluminum carbonates epoxides homogeneous catalysis syn diols |
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