| Literature DB >> 11929246 |
Michael J Martinelli1, 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 Kosmrlj.
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.Entities:
Year: 2002 PMID： 11929246 DOI： 10.1021/ja016031r
Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419