Stereoselective synthesis of enones from the reaction of aldehydes with sterically hindered dimethylaluminum enolates

…, R Nassar, JJ Morris, KW Henderson

Index: Sales, Zachary S.; Nassar, Roger; Morris, J. Jacob; Henderson, Kenneth W. Journal of Organometallic Chemistry, 2005 , vol. 690, # 14 p. 3474 - 3478

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Citation Number: 7

Abstract

The equimolar reaction between Me3Al and the methyl ketones (2, 4, 6-R3–C6H2) C (O) CH3, where R= Me or iPr, results in exclusive formation of the enolization products [{Me2AlOC (2, 4, 6-R3–C6H2) CH2} 2], 1 and 2, upon heating to reflux temperature in toluene solution. The property of Me3Al acting as a base rather than a nucleophile in these reactions is due to the sterically hindered nature of the ketones. Crystallographic analysis ...