Surfactant-type Brønsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water

Seiji Shirakawa; Shū Kobayashi

doi:10.1021/ol062813j

Surfactant-type Brønsted acid catalyzed dehydrative nucleophilic substitutions of alcohols in water

Org Lett. 2007 Jan 18;9(2):311-4. doi: 10.1021/ol062813j.

Authors

Seiji Shirakawa¹, Shū Kobayashi

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 17217292
DOI: 10.1021/ol062813j

Abstract

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].

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzenesulfonates / chemistry*
Benzyl Alcohols / chemical synthesis*
Benzyl Alcohols / chemistry
Catalysis
Glycosylation
Molecular Structure
Stereoisomerism
Surface-Active Agents / chemistry*
Water / chemistry

Substances

Benzenesulfonates
Benzyl Alcohols
Surface-Active Agents
Water
dodecylbenzenesulfonic acid