title: Catalytic Asymmetric Prins Bicyclization for the endo-Selective Formation of 2,6-dioxabicyclo[2.2.2]octanes.
abstract: A new Lewis acid-catalyzed endo-selective Prins bicyclization of γ,δ-unsaturated aldehydes or ketones with a broad range of aldehydes to dioxabicyclo[2.2.2]octanes is disclosed. When using a chiral BINOL-derived N-triflylphosphoramide (NTPA) as catalyst and glyoxylate esters as substrates, the cross-dimerization afford functionalized bicyclic acetals with excellent diastereo- and enantioselectivities.
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P. R. China.|Givaudan Fragrances (Shanghai) Ltd., 298 Li Shi Zhen Road, Shanghai, 201203, P. R. China), Fax.
authors.forename: Jie
authors.initials: J
authors.lastname: Liu
authors.affiliation: Givaudan Fragrances (Shanghai) Ltd., 298 Li Shi Zhen Road, Shanghai, 201203, P. R. China), Fax.
authors.forename: Lijun
authors.initials: L
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P. R. China.
authors.forename: Chao
authors.initials: C
authors.lastname: Wang
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P. R. China.
authors.forename: Demin
authors.initials: D
authors.lastname: Liang
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P. R. China.
authors.forename: Zhiming
authors.initials: Z
authors.lastname: Li
authors.affiliation: Givaudan Fragrances (Shanghai) Ltd., 298 Li Shi Zhen Road, Shanghai, 201203, P. R. China), Fax.
authors.forename: Yue
authors.initials: Y
authors.lastname: Zou
authors.affiliation: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, P. R. China. qrwang@fudan.edu.cn.
authors.forename: Quanrui
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Givaudan Fragrances (Shanghai) Ltd., 298 Li Shi Zhen Road, Shanghai, 201203, P. R. China), Fax. andreas.goeke@givaudan.com.
authors.forename: Andreas
authors.initials: A
authors.lastname: Goeke
keywords: asymmetric catalysis; brønsted acid; organocatalysis; prins reaction; synthetic methods