Highly enantioselective imine cinnamylation with a remarkable diastereochemical switch
John D Huber1, James L Leighton
1Department of Chemistry, Columbia University, New York, New York 10027, USA.
Abstract:
The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastereochemical reversal has been realized whereby either diastereomer may be accessed from the same trans-cinnamylsilane based upon a subtle change to the imine, thus obviating the usual requirement for both the trans- and cis-cinnamylsilanes.
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