Asymmeric Formal [3 + 3]-Cycloaddition Reactions of Nitrones with Electrophilic Vinylcarbene Intermediates

Asymmeric Formal [3 + 3]-Cycloaddition Reactions of Nitrones with Electrophilic Vinylcarbene Intermediates

With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a β-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dir...

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Veröffentlicht in:Journal of the American Chemical Society 2011-10, Vol.133 (41), p.16402-16405
Hauptverfasser: Wang, Xiaochen, Xu, Xinfang, Zavalij, Peter Y, Doyle, Michael P
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Crystallography, X-Ray
Cyclization
Models, Molecular
Molecular Structure
Nitrogen Oxides - chemistry
Organometallic Compounds - chemistry
Oxazines - chemical synthesis
Oxazines - chemistry
Rhodium - chemistry
Stereoisomerism
Vinyl Compounds - chemistry
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Beschreibung
Zusammenfassung:With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a β-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja207664r