Enantioselective Rhodium-Catalyzed [4+2+2] Cycloaddition of Dienyl Isocyanates for the Synthesis of Bicyclic Azocine Rings

Enantioselective Rhodium-Catalyzed [4+2+2] Cycloaddition of Dienyl Isocyanates for the Synthesis of Bicyclic Azocine Rings

A highly enantioselective rhodium-catalyzed [4+2+2] cycloaddition of terminal alkynes and dienyl isocyanates has been developed. The cycloaddition provides a rapid entry to highly functionalized and enantioenriched bicyclic azocines. This reaction represents the first [4+2+2] cycloaddition strategy...

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Veröffentlicht in:Journal of the American Chemical Society 2009-09, Vol.131 (37), p.13250-13251
Hauptverfasser: Yu, Robert T, Friedman, Rebecca Keller, Rovis, Tomislav
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Azocines - chemical synthesis
Azocines - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Isocyanates - chemistry
Rhodium - chemistry
Stereoisomerism
Substrate Specificity
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Zusammenfassung:A highly enantioselective rhodium-catalyzed [4+2+2] cycloaddition of terminal alkynes and dienyl isocyanates has been developed. The cycloaddition provides a rapid entry to highly functionalized and enantioenriched bicyclic azocines. This reaction represents the first [4+2+2] cycloaddition strategy to construct nitrogen-containing eight-membered rings.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja906641d