Pd-catalyzed hydrogenolysis of 4,5-epoxy-2-alkenoates: model study of the acyl side-chain of polyoxypeptin

✍ Scribed by Yasuo Noguchi; Tatsuhiro Yamada; Hiromi Uchiro; Susumu Kobayashi

• Book ID: 104210833
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 161 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01281-8

✦ Synopsis

Palladium-catalyzed hydrogenolysis of 4,5-epoxy-2-alkenoates to 5-hydroxy-2-alkenoates was examined, and it was shown that the (Z)-alkenoate with a bulky substituent at C-4 underwent hydrogenolysis with a decrease in the stereospecificity. Mechanistic considerations and steps for improvement of the stereospecificity are also presented.