Surfactant-type Brønsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water.
A protocol for the dehydrative nucleophilic substitution of benzyl alcohols with a variety of carbon- and heteroatom-centered nucleophiles using dodecylbenzenesulfonic acid (DBSA) as a surfactant-type Brønsted acid catalyst in water has been developed. The reaction system can be applied to the stereoselective C-glycosylation of 1-hydroxy sugars in water. [reaction: see text].
Shirakawa
Seiji
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency, Bunkyo-ku, Tokyo 113-0033, Japan.
Kobayashi
Shū
S
D001557:Benzenesulfonates / Q000737:chemistry*; D001592:Benzyl Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D001557:Benzenesulfonates; D001592:Benzyl Alcohols; D013501:Surface-Active Agents; D014867:Water; C001114:dodecylbenzenesulfonic acid