Development of new chemical reactions that create asymmetric centers heavily depends on the design of new chiral auxiliaries. Access to the chiral auxiliaries is typically hindered by their complex structure. In an effort to reduce the complexity in the preparation of these materials, we are developing unique scaffolds, most of them which are peptidic in nature, that are easy to access and routine to screen. We are also revisiting known and well-established chiral auxiliaries for use in new reactions. For example, the halolactonization of alkene carboxylic acids via the latter two methodologies has yielded ‘proof of principle’ results for continued investigations.