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Increased Yields and Simplified Purification with a Second-Generation Cobalt Catalyst for the Oxidative Formation of trans-THF Rings

Cory Palmer, Nicholas A. Morra, Andrew C. Stevens, Barbora Bajtos, Ben P. Machin and Brian L. Pagenkopf*

*The University of Western Ontario, Department of Chemistry, London, Ontario, N6A 5B7, Email: bpagenkouwo.ca

C. Palmer, N. A. Morra, A. C. Stevens, B. Bajtos, B. P. Machin, B. L. Pagenkopf, Org. Lett., 2009, 11, 5614-5617.

DOI: 10.1021/ol9023375 (free Supporting Information)


Abstract

A second-generation, water-soluble cobalt catalyst for the formation of trans-THF products via the Mukaiyama aerobic oxidative cyclization gives superior yields and enables greatly simplified purification compared to the previous catalysts. Quarternization of the amino group of the ligand with MeI allows a simple, neutral water extraction.

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Key Words

Tetrahydrofurans, Oxygen


ID: J54-Y2009-3620