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Letter

Discovery of a Practical Direct O₂-Coupled Wacker Oxidation with Pd[(−)-sparteine]Cl₂

Supporting Info

Candace N. Cornell and Matthew S. Sigman*

Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850

Org. Lett., 2006, 8 (18), pp 4117–4120

DOI: 10.1021/ol061662h

Publication Date (Web): August 5, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sigman@chem.utah.edu

Abstract

The discovery of a direct O₂-coupled Wacker oxidation with use of balloon pressure of O₂ and low catalyst loading is described. Use of (−)-sparteine as a ligand on Pd prevents olefin isomerization and leads to selective formation of methyl ketones from terminal olefins in good yields. Oxidation of enantiomerically enriched substrates is reported with no observed racemization.

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History

Published In Issue August 31, 2006
Received July 6, 2006

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Letter

Discovery of a Practical Direct O₂-Coupled Wacker Oxidation with Pd[(−)-sparteine]Cl₂