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