4-exo-dig Cyclocarbopalladation: A Straightforward Synthesis of Cyclobutanediols from Acyclic γ-Bromopropargylic Diols under Microwave Irradiation Conditions

✍ Scribed by Christophe Bour; Jean Suffert

• Book ID: 102175815
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 132 KB
• Volume: 2006
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200500813

✦ Synopsis

Abstract

Treatment of acyclic γ‐bromopropargylic diols with tributylstannylated alkynes under palladium catalysis and microwave irradiation conditions gives high yields of the bis(alkylidene)cyclobutanediol derivatives and cyclobutenediols through an efficient 4‐exo‐dig cyclocarbopalladation. The cyclization is general with a wide variety of alkyne derivatives and gives access to new cyclobutane ring systems bearing one exocyclic double bond and one eneyne substituent as well as bicyclic dienes sharing a common double bond that may be of interest for further elaborations of complex molecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)