title: Phosphine-catalyzed [4 + 2] annulation of γ-substituent allenoates: facile access to functionalized spirocyclic skeletons.
abstract: The first phosphine-catalyzed [4 + 2] annulation of γ-substituted allenoates with 2-arylidene-1H-indene-1,3(2H)-diones is disclosed. In the reaction, the γ-substituted allenoate serves as a new type of 1,4-dipolar synthon; this broadens the application of γ-substituted allenoates. This method also offers a powerful approach to the construction of highly substituted spiro[4.5]dec-6-ene skeletons in excellent yields, and with complete regioselectivity and high diastereoselectivity.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University , Tianjin 300071, China.
authors.forename: Erqing
authors.initials: E
authors.lastname: Li
authors.forename: You
authors.initials: Y
authors.lastname: Huang
authors.forename: Ling
authors.initials: L
authors.lastname: Liang
authors.forename: Peizhong
authors.initials: P
authors.lastname: Xie
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D010720:Phosphines; D013141:Spiro Compounds; C044646:phosphine