Au(I)-Catalyzed Annulation of Enantioenriched Allenes in the Enantioselective Total Synthesis of (−)-Rhazinilam
Journal of the American Chemical Society2006Vol. 128(32), pp. 10352–10353
Citations Over TimeTop 1% of 2006 papers
Abstract
Highly stereoselective Au(I)-catalyzed pyrrole additions to enantioenriched allenes afford a unique entry to optically active heterocycles. Asymmetric quaternary carbons can be installed with concurrent heterocycle annulation utilizing this methodology. The enantioenriched allenes are conveniently obtained by catalytic asymmetric acyl halide-aldehyde cyclocondensations and SN2' ring opening of the resulting enantioenriched beta-lactones. An enantioselective total synthesis of (-)-rhazinilam highlights the potential utility of this reaction technology in target-oriented synthesis.
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