Highly enantioselective imine cinnamylation with a remarkable diastereochemical switch.
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.
Huber
John D
JD
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Leighton
James L
JL
D001554:Benzene / Q000737:chemistry; D002934:Cinnamates / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D002934:Cinnamates; D007097:Imines; D001554:Benzene