The Scope and Mechanism of Racemic Carbonate Reactions
We are studying the mechanism for racemic carbonate reactions and exploring the scope of this reaction with respect to substrates, nucleophiles, and leaving groups.
One of our research projects involves the use of a commercially available chiral catalyst in allylic substitution reactions with amines as nucleophiles and carbonates as leaving groups. When racemic carbonates are reacted with one-half equivalents of amines in the presence of this rhodium catalyst, not only are the secondary amine products obtained in high enantioselectivity, the unreacted carbonates are also obtained as a single enantiomer. Thus, this method can be used can be used for the kinetic resolution of racemic carbonates and for the synthesis of secondary amines in large enantiomeric excesses. We are studying the mechanism for this reaction and exploring the scope of this reaction with respect to substrates, nucleophiles, and leaving groups.
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