An Efficient Synthesis of 2,5-Dihydrofuran-Fused Bicyclic Skeletons via the Pd(II)-Catalyzed Tandem-Cyclization Reaction of 1,omega-Bisallenols

作者：Deng Youqian; Shi Yunlong; Ma Shengming^*

来源：Organic Letters, 2009, 11(6): 1205-1208.

DOI：10.1021/ol802794t

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.

• 出版日期2009-3-19
• 单位浙江大学