title: Highly Regio-, Diastereo-, and Enantioselective Gold(I)-Catalyzed Intermolecular Annulations with N-Allenamides at the Proximal C=C Bond.
abstract: A highly enantioselective gold(I)-catalyzed intermolecular annulation of 2-(1-alkynyl)-2-alken-1-ones with N-allenamides is presented. The present work represents the first example of a gold-catalyzed annulation with the proximal C=C bond of an N-allenamide, and is distinctly different from the previously observed annulations at the distal C=C bond. Interestingly, both enantiomers of the products could be obtained in good yields with high regio-, diastereo-, and enantioselectivity by using either diastereomer of a binol-derived phosphoramidite as a chiral ligand.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (China).
authors.forename: Yidong
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (China).
authors.forename: Peichao
authors.initials: P
authors.lastname: Zhang
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (China).
authors.forename: Deyun
authors.initials: D
authors.lastname: Qian
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical, Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (China). jlzhang@chem.ecnu.edu.cn.|State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032 (China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy. jlzhang@chem.ecnu.edu.cn.
authors.forename: Junliang
authors.initials: J
authors.lastname: Zhang
keywords: allenes; cycloaddition; enantioselectivity; gold; heterocycles