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Enantioselective Formation of All-Carbon Quaternary Centers via C-H Functionalization of Methanol: Iridium-Catalyzed Diene Hydrohydroxymethylation

Khoa D. Nguyen, Daniel Herkommer and Michael J. Krische*

*Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States, Email: mkrischemail.utexas.edu

K. D. Nguyen, D. Herkommer, M. J. Krische, J. Am. Chem. Soc., 2016, 138, 14210-14213.

DOI: 10.1021/jacs.6b09333 (free Supporting Information)


Abstract

Insertion of 2-substituted dienes into the methanol C-H bond occurs in a regioselective manner to form all-carbon quaternary centers with excellent levels of enantioselectivity using an iridium-PhanePhos catalyst via methanol dehydrogenation, reversible diene hydrometalation, and regioisomeric formation of allyliridium-formaldehyde pairs.

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Key Words

homoallylic alcohols, alcohols


ID: J48-Y2016