A Diastereoselective Cascade Annulation Approach to Bridged Polycyclic Heterocycles Involving an Unexpected Rearrangement

A diastereoselective cascade annulation between allenoates and in-situ generated isoquinoline N-oxides generating sp3-rich bridged polycyclic heterocycles is disclosed. The reaction proceeds through an unprecedented non-rearomatized rearrangement and allows access to a broad range of bridged heteroc...

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Published inOrganic letters Vol. 25; no. 1; pp. 16 - 20
Main Authors Nikbakht, Ali, Ebrahimi Valdani, Ahmadreza, Zahedian Tejeneki, Hossein, Abbasi Kejani, Alireza, Alavijeh, Nahid S., Bauer, Felix, Darvish, Fatemeh, Breit, Bernhard, Balalaie, Saeed
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.01.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
2-ALKYNYLBENZALDOXIME
SILVER(I)
TANDEM REACTION
GENERATION
VERSATILE BUILDING-BLOCK
TRIFLATE-CATALYZED REACTION
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Summary:A diastereoselective cascade annulation between allenoates and in-situ generated isoquinoline N-oxides generating sp3-rich bridged polycyclic heterocycles is disclosed. The reaction proceeds through an unprecedented non-rearomatized rearrangement and allows access to a broad range of bridged heterocycles in 38–93% yields with excellent functional group tolerance and high diastereoselectivity. Density functional theory calculations provided key insights into the possible reaction pathway and the stereoselectivity of this procedure.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03629