The olefin hydrogenation is extremely important chemical modification used in organic synthesis both on the small and industrial scale. This work describes unusual activity found in applied catalytic system that is very similar to the one reported by Miyaura group. Mentioned group reported mainly hydroboration processes taking place in reaction mixture. Our experimental data suggest that the main reaction in applied catalytic systems is hydrogenation of cycloalkene to cycloalkane (Figure 1).The experimental data obtained for model olefin allowed synthesis of few unique boron derivatives of anti-HIV agent stavudine and thymidine. The hydroboration of stavudine yielded 2',3'-dihydrostavudine under conditions applied. The hydroboration process was found to be present only in oxygen-free system which resulted in the formation of four unique pinacolborano-analogues of thymidine containing boron at 2'- and 3'-positions.

Catalytic hydrogenation and hydroboration of model and biologically active (nucleoside) alkene with borane

243rd National Meeting (2012)

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