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Your search keyword '"Zhu, Shou‐Fei"' showing total 8 results
Start Over Author "Zhu, Shou‐Fei" Journal advanced synthesis & catalysis
8 results on '"Zhu, Shou‐Fei"'

8. Enantioselective Palladium-Catalyzed Ring-Opening Reaction of Azabenzonorbornadienes with Methyl 2-Iodobenzoate: An Efficient Access to cis-Dihydrobenzo[ c]phenanthridinones.

Author

Huang, Kang ‐ Lun, Guo, Cui, Cheng, Li ‐ Jie, Xie, Long ‐ Guan, Zhou, Qi ‐ Lin, Xu, Xiao ‐ Hua, and Zhu, Shou ‐ Fei

Subjects
AMIDATION, PALLADIUM, ZINC powder, ORGANOMETALLIC compounds, RING formation (Chemistry), CHEMICAL reactions
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. [ABSTRACT FROM AUTHOR]

Published
2013
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