As demand for pharmaceuticals and other complex chemical products increases and the state of our environment worsens, eco-friendly methodologies for synthesis are becoming more of a necessity. The majority of waste the pharmaceutical industry produces is from solvents used in organic reactions.  Solvent use can account for up to 90% of waste from industrial pharmaceutical processes. Therefore methods to reduce solvent waste or carryout reactions in environmentally benign solvents would prove to be beneficial to the environment. Recently the use of N-heterocyclic carbenes (NHC's) as organocatalysts has opened up a further arena for the construction of carbon-carbon bonds. N-Heterocyclic carbenes are very versatile catalysts in a variety of transformations. One bench mark transformation within the scope of NHC catalyzed reactions is the benzoin condensation of aldehydes to form an a-hydroxycarbonyl compound. In this presentation we will report the development of an accelerated benzoin condensation in the presence of amphiphilic compounds that produces the a-hydroxycarbonyl compounds in good yield and good enantioselectivities.

Rate acceleration of asymmetric N-heterocyclic carbene reactions in the presence of amphiphiles

246th National Meeting (2013)

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