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

Authors: Ravisekhara P. Reddy and Huw M. L. Davies

J. Am. Chem. Soc.,

2007, 129 (34), 10312–10313


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.

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