Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight
Journal of the American Chemical Society2002Vol. 124(14), pp. 3578–3585
Citations Over TimeTop 19% of 2002 papers
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 V. Khau, Berta Košmrlj
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.
Related Papers
- → Recent Advances in the Regioselective Synthesis of Pyrazoles(2011)73 cited
- → Perfectly Regioselective and Sequential Protection of Glucopyranosides(2010)53 cited
- → Remote substituent effects on regioselectivity in the Pauson–Khand reaction of 2-substituted norbornenes(2001)19 cited
- → N-CHLORO-2,3,4,4,5,6-HEXACHLOROCYCLOHEXA- 2,5-DIENYLIDENEAMINE AS A MILD AND HIGHLY REGIOSELECTIVE CHLORINATING REAGENT(2002)5 cited
- → β-Aminoenones in the regioselective synthesis of 1,3,5-trialkylpyrazoles. The influence of the substituents in the mechanism and the regioselectivity of the reaction(1998)12 cited