Tetrahydroquinolines and Benzazepines through Catalytic Diastereoselective Formal [4 + 2]-Cycloaddition Reactions between Donor–Acceptor Cyclopropenes and Imines

Tetrahydroquinolines and Benzazepines through Catalytic Diastereoselective Formal [4 + 2]-Cycloaddition Reactions between Donor–Acceptor Cyclopropenes and Imines

Regio- and diastereoselective Lewis acid catalyzed cycloaddition reactions between imines and donor–acceptor cyclopropenes generated from silyl-protected enoldiazoacetates provide direct access to stable cyclopropane-fused tetrahydroquinolines and, with cyclopropane ring opening under mild condition...

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Veröffentlicht in:Organic letters 2013-07, Vol.15 (13), p.3278-3281
Hauptverfasser: Truong, Phong M, Mandler, Michael D, Zavalij, Peter Y, Doyle, Michael P
Format: Artikel
Sprache:eng
Schlagworte:
Benzazepines - chemistry
Catalysis
Cycloaddition Reaction
Cyclopropanes - chemistry
Imines - chemistry
Models, Molecular
Molecular Structure
Quinolines - chemical synthesis
Quinolines - chemistry
Stereoisomerism
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Zusammenfassung:Regio- and diastereoselective Lewis acid catalyzed cycloaddition reactions between imines and donor–acceptor cyclopropenes generated from silyl-protected enoldiazoacetates provide direct access to stable cyclopropane-fused tetrahydroquinolines and, with cyclopropane ring opening under mild conditions, to 1H-benzazipine derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401308d