Tertiary Enamide-Promoted Diastereoselective Domino: N-Acyliminium Ion Trapping and Nazarov Cyclization | Zendy

Yongxiang Zheng | Zendy; Lucile Andna | Zendy; Olivia Bistri | Zendy; Laurence Miesch | Zendy

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Tertiary Enamide-Promoted Diastereoselective Domino: N-Acyliminium Ion Trapping and Nazarov Cyclization

Author(s) -

Yongxiang Zheng,

Lucile Andna,

Olivia Bistri,

Laurence Miesch

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02251

Subject(s) - stereocenter , chemistry , domino , ion , trapping , cascade reaction , combinatorial chemistry , conjugated system , cyclic voltammetry , stereochemistry , organic chemistry , electrochemistry , catalysis , electrode , enantioselective synthesis , ecology , polymer , biology

N -Acyliminium ions generated from enamidyl vinyl ketones provided cyclopentenoid-fused diazepines diastereoselectively using BF 3 ·E 2 O in one pot through a domino N -acyliminium ion trapping/Nazarov reaction, simultaneously generating three new stereogenic centers. The particular structural design of the cross-conjugated dienone dictates the torquoselectivity observed in this polarized Nazarov reaction. Various N -bridgehead polycyclic scaffolds of putative pharmacological interest were obtained. Cyclic voltammetry was used to support the preferred reaction sequence within this domino reaction.

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