Related Experiment Videos
Computer-aided design of chiral ligands. Part III. A novel ligand for asymmetric allylation designed using
Marisa C Kozlowski1, Stephen P Waters, Jason W Skudlarek
1Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia 19104, USA. marisa@sas.upenn.edu
Abstract:
[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.