Journal of the American Chemical Society, Vol.130, No.2, 388-388, 2008
Microwave-assisted palladium(0)-catalyzed alkylative Cyclization of allenyl aldehydes leading to 3-substituted 3-cycloalken-1-ols
We have developed an efficient synthetic method for 3-substituted 3-cyclohexe exenols and -cylopantenol based on Pds-catalyzed alkylative, arylative, alkenylative, alkynylative. and borative cyclization reaction of allene-carbonyl compounds. Microwave irradiation increases not only the reaction rate but also the product yield by suppressing formation of hydroarylation byproducts observed in the same catalytic system. Cyclization of optically active 1.3-disubsituted allene aldehyde reveals that the reaction proceeds net through carbopalladation but through "anti-Wacker"-type oxidative addition.