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Using stereocartography for predicting efficacy of stereoinduction by chiral catalysts
Author(s) -
Lipkowitz Kenny B.,
Sakamoto Taka,
Stack Jonathan
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10292
Subject(s) - chemistry , catalysis , enantiomer , quantum chemical , computational chemistry , transition state , transition metal , ligand (biochemistry) , combinatorial chemistry , stereochemistry , organic chemistry , molecule , biochemistry , receptor
Abstract 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. A description of how to treat catalysts with multiple conformations is given. In this article seven catalysts containing a variety of ligand motifs and metals were evaluated. The hypothesis that the region of maximum stereoinduction must be spatially coincident with the site of chemistry for a catalyst to be efficient is upheld. Chirality 15:759–765, 2003. © 2003 Wiley‐Liss, Inc.