title: Enantioselective Palladium-Catalyzed Oxidative Cascade Cyclization of Aliphatic Alkenyl Amides.
abstract: The catalyst system of Pd(TFA)2/(S,S)-diPh-pyrox is reported to promote the highly efficient enantioselective oxidative cascade cyclization of alkene-tethered aliphatic acrylamides under mild aerobic conditions. A series of pyrrolizidine derivatives have been synthesized in good yield and excellent enantioselectivity. Deuterium-labeling experiments have revealed that the reaction proceeded through an anti-aminopalladation (anti-AP) pathway with high selectivity. The transition states for the anti-AP step have been calculated to account for the observed enantioselectivity.
authors.affiliation: Department of Chemistry, The University of Hong Kong , Pokfulam Road, Hong Kong SAR, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Du
authors.affiliation: Department of Chemistry, The University of Hong Kong , Pokfulam Road, Hong Kong SAR, China.
authors.forename: Qiangshuai
authors.initials: Q
authors.lastname: Gu
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong SAR, China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Li
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong SAR, China.
authors.forename: Zhenyang
authors.identifier: 0000-0003-4104-8767
authors.initials: Z
authors.lastname: Lin
authors.affiliation: Department of Chemistry, The University of Hong Kong , Pokfulam Road, Hong Kong SAR, China.
authors.forename: Dan
authors.identifier: 0000-0002-1726-9335
authors.initials: D
authors.lastname: Yang