Using stereocartography for predicting efficacy of stereoinduction by chiral catalysts.

A computational method called stereocartography is used to examine regions around chiral catalysts that are most stereoinducing during Diels-Alder reactions. Geometries and atomic charges of catalysts are first generated quantum mechanically. The transition state of the reaction being catalyzed is then computed quantum mechanically and those enantiomeric transition states are used as probes to determine where around the catalyst stereoinduction is optimal.

Stereocartography: a computational mapping technique that can locate regions of maximum stereoinduction around chiral catalysts.

A hypothesis concerning asymmetric induction by chiral catalysts is posited, tested, and found to be valid. The hypothesis states that chiral catalysts that are efficient at inducing asymmetry will have their region of maximum stereoinduction spatially congruent with the site of chemistry but inefficient catalysts will not. A simple mapping strategy (stereocartography) is used to assess where the region of maximum stereoinduction is located around a given catalyst.