Chirality is a dominant feature in biologically relevant compounds. Our lab is active in the development of new, tunable methods to synthesize chiral products using chiral metal catalysts. To accomplish this goal, we are examining the potential application of nature’s approach to chiral control: the use of accessible and tunable chiral environments, rather than rigidly coordinated (and synthetic) chiral ligands. We have discovered novel methods to generate chiral catalysts based upon ion-pairing with chiral anions or hydrogen bonding with nature’s pool of naturally occurring a-amino acid derivatives. These can in principle provide more accessible methods to generate and tune chiral catalysts. We are currently probing the application of these approaches as alternative classes of reactions, such as those systems where chiral ligands have not proven generally viable, as well as creating new variants of chiral catalytic environments.