Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight

Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols:  Scope and Mechanistic Insight

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 monotosylati...

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Veröffentlicht in:Journal of the American Chemical Society 2002-04, Vol.124 (14), p.3578-3585
Hauptverfasser: 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, Košmrlj, Berta
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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Zusammenfassung: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 pK a 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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja016031r