Highly Enantioselective Dearomatizing Formal [3+3] Cycloaddition Reactions of N-Acyliminopyridinium Ylides with Electrophilic Enol Carbene Intermediates

Extrusion of dinitrogen from enol diazoacetates with a RhII catalyst generates metal enol carbenes. Subsequent vinylogous addition of these to N‐acyliminopyridinium ylides results in an effective formal [3+3] cycloaddition to give highly substituted 1,2,3,6‐tetrahydropyridazines in up to 98 % ee and...

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Veröffentlicht in:	Angewandte Chemie International Edition 2013-11, Vol.52 (48), p.12664-12668
Hauptverfasser:	Xu, Xinfang, Zavalij, Peter Y., Doyle, Michael P.
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation asymmetric catalysis Carbenes Catalysis Catalysts Cycloaddition Cycloaddition Reaction diazo compounds Diazonium Compounds - chemistry enantioselectivity Extrusion heterocycles Imines - chemistry Methane - analogs & derivatives Methane - chemistry Pyridazines - chemical synthesis Pyridazines - chemistry Pyridinium Compounds - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Extrusion of dinitrogen from enol diazoacetates with a RhII catalyst generates metal enol carbenes. Subsequent vinylogous addition of these to N‐acyliminopyridinium ylides results in an effective formal [3+3] cycloaddition to give highly substituted 1,2,3,6‐tetrahydropyridazines in up to 98 % ee and high yield.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201305539