1998 | Sean D. Reilly, Damon R. Click, Steven K. Grumbine, Brian L. Scott, and John G. Watkin
This report, titled "Asymmetric Catalysis in Organic Synthesis," is the final outcome of a three-year Laboratory Directed Research and Development (LDRD) project at Los Alamos National Laboratory (LANL). The project aimed to develop new catalyst systems that can perform chemical reactions in an enantioselective manner, producing only one of the possible optical isomers of the product molecule. The researchers investigated the use of lanthanide metals with both diolate and Schiff-base ligands as catalysts for the enantioselective reduction of prochiral ketones to secondary alcohols. The ligands were synthesized from cheap, readily available starting materials, allowing for modular tailoring of specific groups without repeating the entire synthetic procedure.
Additionally, the team developed a new ligand system for Group IV and lanthanide-based olefin polymerization catalysts. This system, easily prepared from readily available starting materials, offers the ability to rapidly prepare a wide range of closely related ligands differing only in their substitution patterns at an aromatic ring. When attached to a metal center, these ligands have the potential to carry out polymerization reactions in a stereocontrolled manner.
The report highlights the importance of developing new asymmetric catalysts to produce optically pure compounds from optically inactive precursors, which is crucial for the pharmaceutical and fine chemical industries. The research focused on tailoring the Lewis acidity of the metal center and adopting a flexible, modular approach to chiral ligand design. The team optimized the synthesis of optically pure starting materials and successfully scaled up the production of chiral diol ligands. They also explored the binding mode of diolate ligands to metal centers and designed more sterically demanding and rigid ligands to prevent oligomerization and improve enantioselectivity.
The report concludes with discussions on the potential applications of these catalysts in stereospecific polymerization of prochiral olefins, particularly in the production of highly stereoregular polypropylene, which is essential for various consumer products.This report, titled "Asymmetric Catalysis in Organic Synthesis," is the final outcome of a three-year Laboratory Directed Research and Development (LDRD) project at Los Alamos National Laboratory (LANL). The project aimed to develop new catalyst systems that can perform chemical reactions in an enantioselective manner, producing only one of the possible optical isomers of the product molecule. The researchers investigated the use of lanthanide metals with both diolate and Schiff-base ligands as catalysts for the enantioselective reduction of prochiral ketones to secondary alcohols. The ligands were synthesized from cheap, readily available starting materials, allowing for modular tailoring of specific groups without repeating the entire synthetic procedure.
Additionally, the team developed a new ligand system for Group IV and lanthanide-based olefin polymerization catalysts. This system, easily prepared from readily available starting materials, offers the ability to rapidly prepare a wide range of closely related ligands differing only in their substitution patterns at an aromatic ring. When attached to a metal center, these ligands have the potential to carry out polymerization reactions in a stereocontrolled manner.
The report highlights the importance of developing new asymmetric catalysts to produce optically pure compounds from optically inactive precursors, which is crucial for the pharmaceutical and fine chemical industries. The research focused on tailoring the Lewis acidity of the metal center and adopting a flexible, modular approach to chiral ligand design. The team optimized the synthesis of optically pure starting materials and successfully scaled up the production of chiral diol ligands. They also explored the binding mode of diolate ligands to metal centers and designed more sterically demanding and rigid ligands to prevent oligomerization and improve enantioselectivity.
The report concludes with discussions on the potential applications of these catalysts in stereospecific polymerization of prochiral olefins, particularly in the production of highly stereoregular polypropylene, which is essential for various consumer products.