title: Catalytic regioselective sulfonylation of alpha-chelatable alcohols: scope and mechanistic insight.
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.
authors.affiliation: Chemical Process R&D, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285-4813, USA. mjm@lilly.com
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Martinelli
authors.forename: Rajappa
authors.initials: R
authors.lastname: Vaidyanathan
authors.forename: Joseph M
authors.initials: JM
authors.lastname: Pawlak
authors.forename: Naresh K
authors.initials: NK
authors.lastname: Nayyar
authors.forename: Ulhas P
authors.initials: UP
authors.lastname: Dhokte
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Doecke
authors.forename: Lisa M H
authors.initials: LM
authors.lastname: Zollars
authors.forename: Eric D
authors.initials: ED
authors.lastname: Moher
authors.forename: Vien Van
authors.initials: VV
authors.lastname: Khau
authors.forename: Berta
authors.initials: B
authors.lastname: Kosmrlj