A convenient methodology for the chemoselective reduction of a wide variety of functionalized alkenes

✍ Scribed by James H. Babler; Nicholas A. White

• Book ID: 104097165
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 677 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.11.061

✦ Synopsis

An efficient method to effect chemoselective reduction of alkenes (including trisubstituted olefins) possessing various sensitive and/or reducible groups such as acetals, allylic alcohols, benzyl ethers, epoxides, esters, halides, nitriles, and sulfones is reported. The reduction is facile at 0 °C in aqueous N,N-dimethylacetamide containing sodium borohydride in the presence of 15 mol % ruthenium(III) chloride. Regioselective reduction of dienes is also feasible if the double bonds are sufficiently different in their structural environment.