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Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight

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journal contribution
posted on 15.03.2002, 00:00 by Michael J. Martinelli, Rajappa Vaidyanathan, Joseph M. Pawlak, Naresh K. Nayyar, Ulhas P. Dhokte, Christopher W. Doecke, Lisa M. H. Zollars, Eric D. Moher, Vien Van Khau, Berta Košmrlj
This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pKa of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.

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