Development of the First Menthane-Based Chiral Bis(p-allylpalladium) Catalysis: Asymmetric Allylation of Imines

A new ethylidene menthane-based chiral p-allylpalladium complex catalyzes the asymmetric allylation of various imines with allyltributylstannane and 1 equiv. of water to give chiral homoallylamines in good yields and enantioselectivities. The reaction was carried out essentially under neutral conditions and displayed a good transfer of chiral information from the menthane skeleton through the formation of a bis(p-allylpalladium) species. This is the first example of menthane-based chiral bis(p-allylpalladium) catalysis.