Tetrahedron Letters p. 53 - 56 (1996)
Update date:2022-08-04
Topics:
Denis, Cecile
Laignel, Benoit
Plusquellec, Daniel
Le Marouille, Jean-Yves
Botrel, Alain
Highly regioselective reductions of α,β-unsaturated ketones to the corresponding allylic alcohols were performed in essentially quantitative yields in aqueous media containing either glycosidic surfactants or amphiphilic carbohydrates. Reductions of cyclohexanones and cyclohexenones lead under the same conditions, stereoselectively to reduced compounds bearing an equatorial alcohol function. Hydrophobic interactions between amphiphilic carbohydrates and lipophilic substrates were modelized and should account for the observed stereodifferentiation.
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