Enantio‐ and Diastereoselective Synthesis of Chiral Allenes by Palladium‐Catalyzed Asymmetric [3+2] Cycloaddition Reactions |
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Authors: | Prof. Dr. Barry M. Trost Dr. Daniel Zell Dr. Christoph Hohn Dr. Guillaume Mata Autumn Maruniak |
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Affiliation: | Department of Chemistry, Stanford University, Stanford, CA, USA |
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Abstract: | A protocol for the asymmetric synthesis of highly substituted chiral allenes with control of point and axial chirality has been developed. A palladium‐catalyzed [3+2] cycloaddition using readily available racemic allenes gives access to densely functionalized chiral allenes with excellent yields and functional group tolerance. The catalytic asymmetric protocol utilizes a broad range of allenyl TMM (trimethylenemethane) donors to form cyclopentanes, pyrrolidines, and spirocycles with very good control of regio‐, enantio‐, and diastereoselectivity. The chiral allene moiety is shown to be a valuable functional group for rapid elaboration towards complex targets. |
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Keywords: | [3+2] cycloaddition asymmetric catalysis chiral allenes DYKAT reaction mechanism |
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