European Journal of Organic Chemistry p. 2931 - 2938 (2018)
Update date:2022-08-11
Topics:
Suveges, Nicolas S.
Rodriguez, Anderson A.
Diederichs, Carla C.
de Souza, Stefania P.
Le?o, Raquel A. C.
Miranda, Leandro S. M.
Horta, Bruno A. C.
Pedraza, Sérgio F.
de Carvalho, Otavio V.
Pais, Karla C.
Terra, José H. C.
de Souza, Rodrigo O. M. A.
(R)-Propylene carbonate is an important intermediate in the synthesis of tenofovir pro-drugs such as tenofovir alafenamide fumarate (TAF) and tenofovir diisoproyl fumarate (TDF). Independent of the pro-drug type, tenofovir presents a chiral secondary hydroxy derivative, which can be obtained directly from (R)-propylene carbonate. Herein, we report our chemo-enzymatic continuous-flow strategy towards (R)-propylene carbonate starting from a very cheap and renewable raw material, glycerol. We were able to synthesize (R)-propylene carbonate in seven continuous-flow steps, starting from glycerol, in good-to-excellent yields (66–93 %) and excellent selectivity (E > 200).
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