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Regioselectivity Switch: Gold(I)-Catalyzed Oxidative Rearrangement of Propargyl Alcohols to 1,3-Diketones

A. Stephen K. Hashmi*, Tao Wang, Shuai Shi and Matthias Rudolph

*Ruprecht-Karls-Universitšt Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, Email: hashmihashmi.de

A. S. K. Hashmi, T. Wang, S. Shi, M. Rudolph, J. Org. Chem., 2012, 77, 7761-7767.

DOI: 10.1021/jo301381z (free Supporting Information)


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Abstract

A gold(I)-catalyzed oxidative rearrangement of propargyl alcohols provides an efficient and selective route to 1,3-diketones under mild conditions in the presence of pyridine-N-oxides as external oxidants.

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Key Words

Cyclopentanones, Pyridine-N-oxide derivatives, ring expansions


ID: J42-Y2012-3010