Synfacts 2005(0): 0042-0042  
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

Rezensent(en): Hisashi Yamamoto, Matthew Boxer
T. 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  
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Publikationsverlauf

Publikationsdatum:
20. Juli 2005 (online)


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.