title: Highly enantio- and diastereoselective Mannich reactions of glycine Schiff bases with in situ generated N-Boc-imines catalyzed by a cinchona alkaloid thiourea.
abstract: Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable alpha-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active alpha,beta-diamino acid derivatives with up to 99% ee and near-perfect diastereoselection.
authors.affiliation: The Skaggs Institute for Chemical Biology and The Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037.
authors.forename: Haile
authors.initials: H
authors.lastname: Zhang
authors.forename: Salahuddin
authors.initials: S
authors.lastname: Syed
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000577:Amides / Q000737:chemistry; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000577:Amides; D002930:Cinchona Alkaloids; D007097:Imines; D012545:Schiff Bases; D013450:Sulfones; D013890:Thiourea; D005998:Glycine