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Asymmetric Gold-Catalyzed Lactonizations in Water at Room Temperature

Authors


  • We acknowledge financial support for our programs in green chemistry, provided by the NIH (GM86485), the Center for Scientific Computing at the CNSI and MRL [NSF MRSEC (DMR-1121053) and NSF CNS-0960316], and NSF support from the National Center for Supercomputing Applications (NSF TG-CHE100123) utilizing the NCSA Gordon and Blacklight systems. We thank Prof. L. Slaughter (U North Texas) for sharing experimental procedures leading to some of the allenic acids utilized in this work, and Eric D. Slack for technical assistance.

Abstract

Asymmetric gold-catalyzed hydrocarboxylations are reported that show broad substrate scope. The hydrophobic effect associated with in situ-formed aqueous nanomicelles gives good to excellent ee’s of product lactones. In-flask product isolation, along with the recycling of the catalyst and the reaction medium, are combined to arrive at an especially environmentally friendly process.

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