This thesis describes the development of an asymmetric imine cinnamylation reaction of aminophenol and aminomethylphenol imines of aldehydes and the discovery of a new paradigm in asymmetric imine allylation reactions developed in the laboratory of Professor James L. Leighton.

A study of the cinnamylation of aminophenol imines is presented following a brief discussion of previously reported cinnamylation work. The optimization of this reaction produced a highly enantio- and diastereoselective cinnamylation reaction with a broad scope with respect to aldehyde substrates. A similar discussion is then presented regarding the cinnamylation of aminomethylphenol-derived imines giving high yields and selectivities. It was found that the reaction on these very similar substrates gave opposite diastereoselectivity. This allows for the unprecedented advantage of the ability to access both the syn and anti products from a single cinnamylation reagent simply by changing the imine nitrogen protecting group. Within this section is also a discussion of a rapid construction of chiral piperidines in a single step from the cinnamylation products.

Finally the development of a one-pot cross-metathesis/cinnamylation reaction is described. This process allows for the rapid synthesis of a wide variety of products bearing varied aromatic and hetero-aromatic groups adjacent to the carbinamine stereocenter. Coupled with the appropriate selection of imine protecting group, this strategy suggests a new paradigm of imine allylation reactions. Simply by selecting the desired styrene and imine activating group, a wide variety of products can be accessed in either diastereomer from a single readily available allylation reagent. This obviates the need for synthesis of individual reagents for each desired product.