Enantioselective Small Molecule Synthesis by Carbon Dioxide Fixation Using a Dual Brønsted Acid/base Organocatalyst

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2015 Jun 4

PMID 26039818

Citations 11

Authors

Brandon A Vara

Thomas J Struble

Weiwei Wang

Mark C Dobish

Jeffrey N Johnston

Affiliations

Soon will be listed here.

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.

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