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Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Bronsted acid/base organocatalyst.

ABSTRACT: 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.

SUBMITTER: Vara BA

PROVIDER: S-EPMC4708058 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Enantioselective small molecule synthesis by carbon dioxide fixation using a dual Brønsted acid/base organocatalyst.

Vara Brandon A BA Struble Thomas J TJ Wang Weiwei W Dobish Mark C MC Johnston Jeffrey N JN

Journal of the American Chemical Society 20150603 23

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 diox ...[more]

PMID: 26039818

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