Computer-aided design of chiral ligands. Part III. A novel ligand for asymmetric allylation designed using computational techniques.
[reaction: see text] Computer-aided design protocols to identify new chiral ligands for reactions proceeding through well-defined transition states are outlined. Ligand families are discovered via computational screening of large structural databases such as the Cambridge Structural Database. Using this method, a novel cis-decalin ligand has been identified as a chiral auxiliary for the allylboration of aldehydes. Synthesis, resolution, and evaluation revealed that this new auxiliary provided the aldehyde facial approach upon which the design was predicated.
Kozlowski
Marisa C
MC
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia 19104, USA. marisa@sas.upenn.edu
Waters
Stephen P
SP
Skudlarek
Jason W
JW
Evans
Catherine A
CA
D017076:Computer-Aided Design; D016208:Databases, Factual; D015195:Drug Design; D004353:Drug Evaluation, Preclinical; D008024:Ligands; D015394:Molecular Structure; D012984:Software; D013237:Stereoisomerism
D008024:Ligands