SmI2-Induced highly regioselective reduction of α,β-epoxy esters and γ,δ-epoxy-α,β-unsaturated esters. An efficient route to optically active β-hydroxy and δ-hydroxy esters

✍ Scribed by Kenji Otsubo; Junji Inanaga; Masaru Yamaguchi

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 233 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96532-8

✦ Synopsis

o!,P-Epoxy esters were rapidly reduced at room temperature to yield P-hydroxy esters with retention of the configurations at the P-carbon atoms by using Sm12-THF-HMPA system in the presence of N,N-dimethylaminoethanol (DMAE). to the synthesis of vinylogous &'-hydroxy esters. The conditions were successfully applied Esters having a hydroxyl function at their CC-, p-, r-, or &-position not only constitute an important class of natural products but also serve as useful intermediates in organic synthesis.