Fig. 5: Hydroborylation and homologation of cyclopentenes 3. | Communications Chemistry

Fig. 5: Hydroborylation and homologation of cyclopentenes 3.

From: Catalytic asymmetric synthesis of carbocyclic C-nucleosides

Fig. 5

Elaboration of cyclopentenes 3 to RNA analogs. Reaction Conditions - Hydroborylation: 3 (1 equiv), pinacol borane (2 equiv), [Rh(PPh3)Cl] (2.5 mol%), CsCO3 (1 equiv), THF, 50 °C, 16 h. Homologation: 4 (1 equiv), iodochloromethane (3 equiv), nBuLi (2.5 equiv), THF, −78 °C to rt, 18 h.

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