Alkyl Metal Asymmetric Reduction. 12. Optically Active Phenylalkanes from Organoaluminum Derivatives and Aliphatic Ketones

Article abstract of DOI:10.1021/jo00143a033

The reaction of β-branched alkylaluminum dichloride with some aliphatic ketones has been studied in various solvents at room temperature.In benzene, the organoaluminum derivative rapidly reduces the ketone with formation of the alkoxyaluminum dichloride, which slowly alkylates the benzene to the corresponding phenylalkane.When optically active (2-methylbutyl)aluminum dichloride is used, both the carbinol from hydrolysis of the alkoxy aluminum species and the phenylalkane are optically active and of opposite absolute configuration.The overall results are also interpreted on the basis of previous findings, and a mechanism that accounts f or the formation of the optically active phenylalkanes is presented.