Asymmetric Synthesis of Tropanes by Rhodium-Catalyzed [4 + 3] Cycloaddition

Asymmetric Synthesis of Tropanes by Rhodium-Catalyzed [4 + 3] Cycloaddition

Rhodium-catalyzed [4 + 3] cycloaddition between methyl 2-(siloxy)vinyldiazoacetate and pyrroles results in the enantioselective synthesis of highly functionalized 8-azabicyclo[3.2.1]octa-2,6-dienes (tropanes). The reaction proceeds via a rhodium−carbenoid intermediate and involves a tandem cycloprop...

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Veröffentlicht in:Journal of the American Chemical Society 2007-08, Vol.129 (34), p.10312-10313
Hauptverfasser: Reddy, Ravisekhara P, Davies, Huw M. L
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Molecular Structure
Rhodium - chemistry
Stereoisomerism
Tropanes - chemical synthesis
Tropanes - chemistry
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Zusammenfassung:Rhodium-catalyzed [4 + 3] cycloaddition between methyl 2-(siloxy)vinyldiazoacetate and pyrroles results in the enantioselective synthesis of highly functionalized 8-azabicyclo[3.2.1]octa-2,6-dienes (tropanes). The reaction proceeds via a rhodium−carbenoid intermediate and involves a tandem cyclopropanation/Cope rearrangement mechanism. The optimum chiral dirhodium catalyst for this transformation is the adamantyl glycine-derived complex, Rh2(S-PTAD)4.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja072936e