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Synfacts 2005(0): 0042-0042
DOI: 10.1055/s-2005-869920
DOI: 10.1055/s-2005-869920
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
‘One-Pot’ Zr-Catalyzed Asymmetric Carboalumination-Pd Cross-Coupling
Contributor(s): Hisashi Yamamoto, Matthew BoxerT. Novak, Z. Tan, B. Liang, E. Negishi*
Purdue University, West Lafayette, USA
All-Catalytic, Efficient, and Asymmetric Synthesis of α,ω-Diheterofunctional Reduced Polypropionates via ‘‘One-Pot’’ Zr-Catalyzed Asymmetric Carboalumination-Pd-Catalyzed Cross-Coupling Tandem Process
J. Am. Chem. Soc. 2005, 127: 2838-2839
Purdue University, West Lafayette, USA
All-Catalytic, Efficient, and Asymmetric Synthesis of α,ω-Diheterofunctional Reduced Polypropionates via ‘‘One-Pot’’ Zr-Catalyzed Asymmetric Carboalumination-Pd-Catalyzed Cross-Coupling Tandem Process
J. Am. Chem. Soc. 2005, 127: 2838-2839
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
carboalumination - polypropionates - zinc
Significance
An efficient all-catalytic asymmetric protocol for the synthesis of α,ω-diheterofunctional reduced polypropionates in one pot has been achieved. Starting from inexpensive styrene, asymmetric Zr-catalyzed carbo-alumination followed by Pd-catalyzed vinylation of the isoalkylalanes allows for the construction of reduced polypropionate chains.
Comment
The two catalytic steps have been coupled in a nice manner allowing for the one pot construction of enantioenriched polypropionates. As the authors mention, there is room for further improvements, but this protocol likely will make the synthesis of reduced polypropionates more efficient and satisfactory.