Catalytic regioselective sulfonylation of α-chelatable alcohols: scope and mechanistic insight

MJ Martinelli, R Vaidyanathan, JM Pawlak…

文献索引：Martinelli, Michael J.; Vaidyanathan, Rajappa; Pawlak, Joseph M.; Nayyar, Naresh K.; Dhokte, Ulhas P.; Doecke, Christopher W.; Zollars, Lisa M. H.; Moher, Eric D.; Khau, Vien Van; Kosmrlj, Berta Journal of the American Chemical Society, 2002 , vol. 124, # 14 p. 3578 - 3585

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被引用次数: 130

摘要

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 p K a of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of ...