Silicon‐Induced Diastereoselectivity of the Catalyzed Phosphorylation of 1‐(Perfluoroalkyl)‐ω‐(trialkylsilyl)alkan‐1‐ols.

Abstract

Organo-phosphorus compounds S 0080Silicon-Induced Diastereoselectivity of the Catalyzed Phosphorylation of 1-(Perfluoroalkyl)-ω-(trialkylsilyl)alkan-1-ols. -The stereoselectivity of phosphorylation of alcohols is strongly influenced by the substrate structure. Three structural elements are necessary to achieve diastereoselective phosphorylation. These are, firstly, a silicon atom in β-position to the alcohol, secondly, a methyl group at the phosphorus atom [cf. (IIIa) vs. (IIIe)] and, thirdly, a bulky polyfluoroalkyl group at the α-position [cf. (IIIb) vs. (IIIi)]. -(MOLCHANOVA*, G. N.; SHCHERBINA, T. M.; PETROVSKII, P. V.; KUDRYAVTSEV, I. Y.; ZAKHAROV, L. S.; Russ.