Phosphine-Free Palladium-Catalyzed Allene Carbopalladation/Allylic Alkylation Domino Sequence: A New Route to 4-(α-Styryl) γ-Lactams

✍ Scribed by Claire Kammerer; Guillaume Prestat; David Madec; Giovanni Poli

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 244 KB
• Volume: 15
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200900184

✦ Synopsis

Abstract

Free to decide: Various 4‐(α‐styryl) γ‐lactams are synthesized in 61–88 % yield by a phosphine‐free palladium‐catalyzed carbopalladation/allylic alkylation domino sequence (see scheme). The cyclization is totally regio‐ and diastereoselective in favor of the 3,4‐trans‐disubstituted γ‐lactam. The process is successfully applied to the synthesis of a new aza analogue of the naturally occurring lignan (+)‐oxo‐parabenzlactone.magnified image