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- Title
Enantioselective Palladium-Catalyzed Ring-Opening Reaction of Azabenzonorbornadienes with Methyl 2-Iodobenzoate: An Efficient Access to cis-Dihydrobenzo[ c]phenanthridinones.
- Authors
Huang, Kang ‐ Lun; Guo, Cui; Cheng, Li ‐ Jie; Xie, Long ‐ Guan; Zhou, Qi ‐ Lin; Xu, Xiao ‐ Hua; Zhu, Shou ‐ Fei
- Abstract
The palladium-catalyzed asymmetric ring-opening (ARO) reaction of azabenzonorbornadienes with iodobenzoate derivatives was realized by using chiral spirophosphine ligands with zinc powder as a reducing reagent. Various enantiomerically enriched cis-dihydrobenzo[ c]phenanthridinones, the core structure of numerous chiral natural products, were prepared by the ARO reaction and tandem amidation from easily obtained starting materials with favorable enantioselectivity (up to 86% ee) under mild reaction conditions. The present palladium-catalyzed ARO reaction avoids the direct use of organometallic reagents, enables tandem cyclization, and thus improves synthetic efficiency. The formal total synthesis of a chiral natural product, (+)-chelidonine, was accomplished with the ARO reaction as a key step, which demonstrates the potential synthetic applications of the present methodology.
- Subjects
AMIDATION; PALLADIUM; ZINC powder; ORGANOMETALLIC compounds; RING formation (Chemistry); CHEMICAL reactions
- Publication
Advanced Synthesis & Catalysis, 2013, Vol 355, Issue 14/15, p2833
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201300452