Functionalized Cyclobutanes via Heck Cyclization

Innitzer, Anna; Brecker, Lothar; Mulzer, Johann.   

Organic Letters  (2007),  9(22),  4431-4434.

Heck-type 4-exo-trig cyclization of linear 2-enol triflate-1,5-hexadienes provides functionalized methylene cyclobutanes. Intramolecular palladium coordination can initiate β-hydride elimination leading to 1,2-dimethylene cyclobutane derivatives, which are obtained with high selectivity if substrates having a geminal diphenyl group at Cα are used. In parallel, formal 5-endo-trig cyclization and β-hydride elimination form 1-methylene cyclopent-2-en derivatives.