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Dibutyltin Oxide Catalyzed Selective Sulfonylation of α-Chelatable Primary Alcohols

Michael J. Martinelli*, Naresh K. Nayyar, Eric D. Moher, Ulhas P. Dhokte, Joseph M. Pawlak and Rajappa Vaidyanathan

*Chemical Process R&D, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285-4813

M. J. Martinelli, N. K. Nayyar, E. D. Moher, U. P. Dhokte, J. M. Pawlak, R. Vaidyanathan, Org. Lett., 1999, 1, 447-450.

DOI: 10.1021/ol990658l

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Dibutyltin oxide catalyzes a selective and rapid sulfonylation of glycols at the primary alcohol in the presence of stoichiometric p-toluenesulfonyl chloride and triethylamine in CH2Cl2. α-Heterosubstituted primary alcohols appeared optimal for best results, supporting the intermediacy of a five-membered chelate.

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Key Words


ID: J54-Y1999