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Journals and Conferences
Dynamic resolution has been studied as a method for the asymmetric synthesis of 2-substituted pyrrolidines. Highly enantioselective electrophilic substitutions of racemic 2-lithiopyrrolidines in the presence of a chiral ligand have been achieved. The organolithium compounds were prepared by tin-lithium exchange from the corresponding tributylstannanes and… (More)
Asymmetric substitution of the organolithium derived either from N-Boc-2-tributylstannylpyrrolidine by tin-lithium exchange or from N-Boc-pyrrolidine by deprotonation occurs in the presence of a commercially available chiral diamine ligand with high levels of enantioselectivity by a dynamic kinetic resolution pathway.
Treatment of a geminal pivaloxy xanthate, prepared by an intermolecular radical addition of a xanthate to vinyl pivalate, gives a 1,3-dithietanone, a little known class of compounds.
Kinetics experiments have been used to establish the free energy, enthalpy, and entropy of activation for the enantiomerization of three structural classes of 2-lithiopyrrolidines. We find that alpha-aminoorganolithiums chelated by a N-methoxyethyl or N-Boc group have a barrier to enantiomerization (DeltaG++) 2-3 kcal/mol lower than that of unstabilized… (More)
In model studies towards the synthesis of kirkine, the carbon skeleton was constructed using a radical cascade reaction. Two different approaches towards the synthesis have been examined as well as the regioselectivity of the radical cyclisation.