Communication

Enantioselective Small Molecule Synthesis by Carbon Dioxide Fixation using a Dual Brønsted Acid/Base Organocatalyst

Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, United States
J. Am. Chem. Soc., 2015, 137 (23), pp 7302–7305
DOI: 10.1021/jacs.5b04425
Publication Date (Web): June 3, 2015
Copyright © 2015 American Chemical Society

Abstract

Abstract Image

Carbon dioxide exhibits many of the qualities of an ideal reagent: it is nontoxic, plentiful, and inexpensive. Unlike other gaseous reagents, however, it has found limited use in enantioselective synthesis. Moreover, unprecedented is a tool that merges one of the simplest biological approaches to catalysis—Brønsted acid/base activation—with this abundant reagent. We describe a metal-free small molecule catalyst that achieves the three component reaction between a homoallylic alcohol, carbon dioxide, and an electrophilic source of iodine. Cyclic carbonates are formed enantioselectively.

Supporting Information


Experimental procedures and spectroscopic data for all new compounds, and X-ray data (cif) for 2a. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.5b04425.

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Article Views: 5,649 Times
Received 28 April 2015
Published online 3 June 2015
Published in print 17 June 2015
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