Predicting the stereochemistry of diphenylphosphino benzoic acid (DPPBA)-based palladium-catalyzed asymmetric allylic alkylation reactions: a working model.
Palladium-catalyzed asymmetric allylic alkylation has proven to be a powerful method for the preparation of a wide variety of chiral compounds and the rapid assembly of complex molecular architecture from simple starting materials. While many types of catalyst systems have been successfully employed with certain systems, diphenylphosphino benzoic acid (DPPBA) based ligands have found use over a broad range of substrate classes. This Account highlights the mechanistic aspects considered when designing reactions with DPPBA-based ligands and presents a working model for the a priori prediction of their stereochemical outcome.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Machacek
Michelle R
MR
Aponick
Aaron
A
D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D008956:Models, Chemical; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D001549:Benzamides; D008024:Ligands; D010720:Phosphines; D010165:Palladium