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Functionalized Dihydro/Tetrahydrobenzo[ a ]Fluorenes via Interrupted Iso ‐Nazarov Reaction

Year: 2025

Type: article

Abstract: Under the catalysis of p-TsOH immobilized on silica (PTS-Si), the iso-Nazarov reaction of (E)-(2-stilbenyl)methanol/(E)-(2-stilbenyl)imine tosylate bearing a styrene moiety forged the corresponding [5/6] systems with the exclusive trans relationship at the two newly formed adjacent stereogenic centers. The ensuing "interrupted" nucleophilic addition by the pendent styrenyl olefin furnished the dihydro-11H-benzo[a]fluorene with the exclusive cis stereocontrol at the two-carbon ring junction. Thus, from non-chiral starting materials, the interrupted iso-Nazarov reaction formed two rings and provided the olefin moiety, which can be functionalized to other groups/systems possessing one to two additional chiral centers. Up to five contiguous stereogenic centers on the tetrahydrobenzo[a]fluorene could be constructed efficiently.

Source: Chemistry - An Asian Journal

DOI: 10.1002/asia.70489

Authors: Tanawat Phumjan, Kasam Poonswat, Chatphorn Theppitak, Paratchata Batsomboon, Somsak Ruchirawat, Poonsakdi Ploypradith

Institutions: Chulabhorn Graduate Institute, Chulabhorn Research Institute, Ministry of Higher Education, Science, Research and Innovation

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

OpenAlex ID: W4417020506

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Cites: 66

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