title: A synthetic strategy for polyfunctionalized bicyclo[3.3.1]nonanes based on a tandem three-component [3 + 2] cycloaddition of alpha-cinnamoyl ketene-S,S-acetals with oxalyl chloride.
abstract: A simple and highly efficient three-component reaction of the readily available alpha-cinnamoyl ketene-S,S-acetals 1 with oxalyl chloride has been developed and the corresponding gamma-alkylidenebutenolides 2 were obtained stereospecifically in excellent yields under very mild conditions. On the basis of this reaction, a series of highly functionalized bicyclo[3.3.1]nonanes 3 were constructed in good to high yields in an atom-economic manner with good diastereoselectivity via a BF3.OEt2-mediated novel tandem double cyclization of gamma-alkylidenebutenolides 2 under very mild conditions.
authors.affiliation: Department of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China. zhaoyl351@nenu.edu.cn
authors.forename: Yu-Long
authors.initials: YL
authors.lastname: Zhao
authors.forename: Li
authors.initials: L
authors.lastname: Chen
authors.forename: Shao-Chun
authors.initials: SC
authors.lastname: Yang
authors.forename: Cui
authors.initials: C
authors.lastname: Tian
authors.forename: Qun
authors.initials: Q
authors.lastname: Liu