Control of selectivity in the generation and reactions of oxonium ylides

Control of selectivity in the generation and reactions of oxonium ylides

Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (27), p.7623-7625
Hauptverfasser: Jaber, Deana M, Burgin, Ryan N, Hepler, Matthew, Zavalij, Peter, Doyle, Michael P
Format: Artikel
Sprache:eng
Schlagworte:
Acetoacetates - chemistry
Aromatic compounds
Bridged Bicyclo Compounds - chemistry
Catalysis
Models, Molecular
Pyrones - chemistry
Rhodium - chemistry
Selectivity
Stereoisomerism
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Beschreibung
Zusammenfassung:Dirhodium catalyzed reactions of aryl-substituted tetrahydropyranone diazoacetoacetates produce ylide intermediates that unexpectedly yield two oxabicyclo[4.2.1]-nonane diastereoisomers, but a single diastereoisomer is formed by increasing the steric bulk of the aryl substituent.
ISSN:1359-7345
1364-548X
DOI:10.1039/c1cc12443a