An efficient synthesis of chiral, nonracemic isopropyl alkenylmethylphosphinates via palladium route

✍ Scribed by Yuanyao Xu; Hengxu Wei; Jing Zhang; Guohua Huang

• Book ID: 104227081
• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 205 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95287-0

✦ Synopsis

Enantiomerically pure (S)-and (R)-isopropyl alkenylmethylphosphinates were obtained from the reaction of (R)-and (S)-isopropyl methylphosphinates, respectively, with alkenyl bromides via palladium-catalyzed formation of carbon-phosphorus bond. Optically active alkenylalkylphosphinates are largely unknown'), although their racemates are useful intermediates for the synthesis of herbicides2). Recently, we have studied the stereochemistry at the phosphorus atom during palladium-catalyzed formation of carbon-phosphorus bonds and found that optically active (R)-(+)-isopropyl methylphosphinate (la) underwent the reaction with bromobenzene in the presence of triethylamine to afford (S)-(-)-isopropyl