Aldol Reaction – Simple Diastereoselectivity Trans give Anti

Trans Lithium enolates (E) generally give Anti Aldol products

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In an aldol reaction, trans enolates prefer to form anti aldols. The reaction proceeds via a chair like transition state where the aldehyde chooses to react with the methyl group equatorial. As the enolate has no choice over its orientation, only an anti product is possible.

C. H. Heathcock, C. T. Buse, W. A. Kleschick, M. C. Pirrung, J. E. Sohn and J. Lampe, J. Org. Chem., 1980, 45, 1066–1081.

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