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Updated: Jul 18, 2026

In Situ SIMS and IR Spectroscopy of Well-defined Surfaces Prepared by Soft Landing of Mass-selected Ions
Published on: June 16, 2014
Catalytic regioselective sulfonylation of alpha-chelatable alcohols: scope and mechanistic insight
Michael J Martinelli1, Rajappa Vaidyanathan, Joseph M Pawlak
1Chemical Process R&D, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285-4813, USA. mjm@lilly.com
Abstract:
This paper describes a convenient protocol for the regioselective sulfonylation of alpha-chelatable alcohols. Typically, the reaction of alpha-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et(3)N in the presence of 2 mol % of Bu(2)SnO leads to rapid, regioselective, and exclusive monotosylation. The pK(a) of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of (119)Sn NMR studies.
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