Stereoselective synthesis of dibenzoxapine containing tetrasubstituted exocyclic alkenes via cascade methylboronic acid coupling reactions

✍ Scribed by Hannah Yu; Rachel N. Richey; Javier Mendiola; Marta Adeva; Carmen Somoza; Scott A. May; Matthew W. Carson; Michael J. Coghlan

• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 131 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.01.099

✦ Synopsis

A stereoselective method for the preparation of dibenzoxapine containing tetrasubstituted exocyclic E-alkenes has been developed. The key reaction involves an intramolecular cyclocarbopalladation of alkynes to form a vinylpalladium species and subsequently coupling the vinylpalladium with methylboronic acid. The approach provides a straightforward method for the synthesis of tetrasubstituted exocyclic E-alkenes.