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Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic cis ‐Diol Scaffolds
Author(s) -
Laserna Victor,
Fiorani Giulia,
Whiteoak Christopher J.,
Martin Eddy,
EscuderoAdán Eduardo,
Kleij Arjan W.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406645
Subject(s) - synthon , chemoselectivity , diol , catalysis , chemistry , yield (engineering) , carbon dioxide , combinatorial chemistry , carbonate , metal , organic chemistry , materials science , metallurgy
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 CO 2 as a temporary protecting group.