In a search for a vinylogous version of Cram's rule, 1,4-diphenylbut-2-ene-1,4-dione (5), 4-methoxy-1,4-diphenylbut-2-en-1-one (9), and hex-3-ene-2,5-dione (13) are found to be reduced with low or negligible diastereoselectivity. Similarly, the phenyl Grignard reagent showed no diastereoselectivity in its reaction with 4-methoxy-4-phenylbut-2-enal (12)
I. Fleming, H. Kühne and K. Takaki, J. Chem. Soc., Perkin Trans. 1, 1986, 725 DOI: 10.1039/P19860000725
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