An efficient synthesis of 2,5-dihydrofuran-fused bicyclic skeletons via the Pd(II)-catalyzed tandem-cyclization reaction of 1,omega-bisallenols.
A palladium(II)-catalyzed tandem double-cyclization reaction of 1,omega-bisallenols was developed to form 2,5-dihydrofuran-fused bicyclic skeletons. With "unsymmetric" substrates, the reaction may also be realized with one hydroxyl group being protected as the acetate. Optically active bicyclic products were prepared by applying the Novozym-435 catalyzed kinetic resolution and the tandem double cyclization of these optically active allenol-allenyl acetates. The reaction may proceed via an oxypalladation, insertion, and elimination process.
Deng
Youqian
Y
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China.
Shi
Yunlong
Y
Ma
Shengming
S
D000438:Alcohols / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*
D000438:Alcohols; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D010165:Palladium