A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates
Brian W. Michel, Andrew M. Camelio, Candace N. Cornell and Matthew S. Sigman*
*Department of Chemistry, University of Utah, 315 S 1400 E, Salt Lake City, Utah 84112-085, Email: sigmanchem.utah.edu
B. W. Michel, A. M. Camelio, C. N. Cornell, M. S. Sigman, J. Am. Chem. Soc., 2009, 131, 6076-6077.
DOI: 10.1021/ja901212h (free Supporting Information)
Utilizing the rapidly synthesized Quinox ligand and commercially available aqueous TBHP, a Wacker-type oxidation efficiently converts even traditionally challenging substrates such as protected allylic alcohols to the corresponding oxidized products. Enantioenriched substrates undergo oxidation with complete retention of enantiomeric excess.
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R. J. DeLuca, J. L. Edwards, L. D. Steffens, B. W. Michel, X. Qiao, C. Zhu, S. P. Cook, M. S. Sigman, J. Org. Chem., 2013, 78, 1682-1683.