Alkene asymmetric hydration

Fig. 3.30. Asymmetric hydration of an achiral alkene via hydroboration/oxidation/hydro lysis AFa corresponds to the extent of reagent control of diastereoselectivity.

Schnapperelle, 1., Hummel, W., and Groger, H. (2012) Eormal asymmetric hydration of non-activated alkenes in aqueous medium through a chemoenzymatic catalytic system . 

Lei X, Bin J, Li T, Xiao FJ, Mei YH, Ying YJ (2004) Asymmetric hydration of alkenes catalyzed by wool-palladium complex. Polym Adv Technol 15 346-349... 

Nitroalkanes are a particularly useful source of stabilised carbanions for the asymmetric addition to electron-poor alkenes. This type of nucleophiles has been added to cyclic and acyclic a,p-unsaturated enones in the presence of a novel class of organocatalysts, such as chiral a-aminophosphonates.This study revealed that the hydrate salt of a pyrrolidine-based catalyst bearing a phosphonate group, depicted in Scheme 1.14, was found to be the best catalytic species, providing, in the presence of tra i-2,5-dimethylpiperazine as an additive, moderate to good results for a range of substrates, as summarised in Scheme 1.14. 

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