Au(I)-Catalyzed Annulation of Enantioenriched Allenes in the Enantioselective Total Synthesis of (−)-Rhazinilam
- 22 July 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (32) , 10352-10353
- https://doi.org/10.1021/ja0629110
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 β-lactones. An enantioselective total synthesis of (−)-rhazinilam highlights the potential utility of this reaction technology in target-oriented synthesis.Keywords
This publication has 8 references indexed in Scilit:
- Catalysts for Suzuki−Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand StructureJournal of the American Chemical Society, 2005
- Modern Allene ChemistryPublished by Wiley ,2004
- Transition-Metal-Catalyzed Addition of Heteroatom−Hydrogen Bonds to AlkynesChemical Reviews, 2004
- On Inventing Reactions for Atom EconomyAccounts of Chemical Research, 2002
- Catalytic Asymmetric Propionate Aldol Reactions via Acyl Halide−Aldehyde CyclocondensationsOrganic Letters, 2000
- Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensations. A Strategy for Enantioselective Catalyzed Cross Aldol ReactionsJournal of the American Chemical Society, 1999
- Preparation of 3,3-difluoroacrylic acid derivatives by dehydrohalogenation of activated acyl compounds. Synthesis of two potential precursors to difluoropropadienoneThe Journal of Organic Chemistry, 1991
- Facile introduction of ester groups into the pyrrole nucleus via trichloroacetylation and alcoholysisThe Journal of Organic Chemistry, 1972