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Synfacts 2007(3): 0277-0277  
DOI: 10.1055/s-2007-968269
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Regioselective Negishi Carboaluminations

Contributor(s): Mark Lautens, Praew Thansandote
B. H. Lipshutz*, T. Butler, A. Lower
University of California, Santa Barbara, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

A zirconocene catalyst was discovered to perform Negishi carboaluminations with a variety of alkynes and electrophiles in high yields and excellent regioselectivities and stereoselecti­vities favoring the E-isomer (usually >99:1 E/Z). Tandem carboalumination-1,4-addition and carboalumination-C-C bond formation were also reported with high yields and regioselectivities. This methodology for the synthesis of the important coenzyme Q10 was successfully extended.