Chiral butenolides as dienophiles in Diels-Alder cycloadditions

✍ Scribed by R.M. Ortuño; J. Corbera; J. Font

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 194 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(86)80054-5

✦ Synopsis

Differently substituted chiral butenolides, prepared from D-ribonolactone react atadiene at 210" affording enantiomerically pure bicycloadducti as single dialtereoisomers, in good yields. The ability of protoanemonin (formed in some pyrolytic reaction conditions) to react regiospecifically at the exocyclic double bond, to give spirolactones, isshown. The Diels-Alder cycloaddition remains today one of the most powerful synthetic methods.