title: Phosphine-catalyzed domino reactions: a route to functionalized bicyclic skeletons.
abstract: A novel strategy that involves phosphine-catalyzed sequential [2+3] and [3+2] annulation reactions was developed. In this domino reaction, γ-substituted allenoates were used as novel C4 synthons, and the bicyclic cyclopenta[b]dihydrofuran derivatives were produced in good to excellent diastereoselectivities and yields under mild conditions. Furthermore, preliminary studies on an asymmetric variant of this reaction proceeded with moderate enantioselectivity.
authors: State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071 (P. R. China), Fax: (+86) 22-23503627.
authors: Erqing
authors: E
authors: Li
authors: You
authors: Y
authors: Huang
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D005663:Furans; D010720:Phosphines; C044646:phosphine
keywords: allenes; diastereoselectivity; domino reactions; fused-ring systems; phospines; sequential annulation