84207-31-8Relevant academic research and scientific papers
Catalytic regioselective sulfonylation of α-chelatable alcohols: Scope and mechanistic insight
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
, p. 3578 - 3585 (2007/10/03)
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.
