ChemInform Abstract: Palladium-Catalyzed Intramolecular Cyclization of Olefinic Propargylic Carbonates and Application to the Diastereoselective Synthesis of Enantiomerically Pure (-)-α-Thujone.

✍ Scribed by W. OPPOLZER; A. PIMM; B. STAMMEN; W. E. HUME

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 37 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199730047

✦ Synopsis

Palladium-Catalyzed Intramolecular Cyclization of Olefinic Propargylic Carbonates and Application to the Diastereoselective Synthesis of Enantiomerically Pure (-)-α-Thujone.

-Pd/P(2-furyl)3 catalyzed title reactions afford intermediate palladium( alkenyl)bicyclo(3.1.0)hexanes, which can be trapped by hydride donor, carbonylated or cross-coupled with organometallic reagents. The potential of the tandem double cyclization/crosscoupling is demonstrated by its application towards the first enantiospecific synthesis of the monoterpene thujone (XIII). -(OPPOLZER, W.; PIMM, A.;