Pd and Mo Catalyzed Asymmetric Allylic Alkylation

Abstract

The ability to control the alkylation of organic substrates becomes ever more powerful by using metal catalysts. Among the major benefits of metal catalysis is the possibility to perform such processes asymmetrically using only catalytic amounts of the chiral inducing agent which is a ligand to the metal of the catalyst. A unique aspect of asymmetric metal catalyzed processes is the fact that many mechanisms exist for stereoinduction. Furthermore, using the same catalyst system, many types of bonds including but not limited to C-C, C-N, C-O, C-S, C-P, and C-H can be formed asymmetrically. An overview of this process using palladium and molybdenum based metals being developed in my laboratories and how they influence strategy in synthesizing bioactive molecular targets is presented.

Fig. 1

Typical ligands for Pd AAA

Fig. 2

Structural Representatives of Active Catalysts

Fig. 3

Typical Ligands for Mo AAA

Scheme 1

Mechanism of Pd Catalyzed Allylic Alkylation