title: Stereoselective synthesis of functionalized cyclic amino acid derivatives via a [2,3]-Stevens rearrangement and ring-closing metathesis.
abstract: Unnatural cyclic amino acids are valuable tools in biomedical research and drug discovery. A two-step stereoselective strategy for converting simple glycine-derived aminoesters into unnatural cyclic amino acid derivatives has been developed. The process includes a palladium-catalyzed tandem allylic amination/[2,3]-Stevens rearrangement followed by a ruthenium-catalyzed ring-closing metathesis. The [2,3]-rearrangement proceeds with high diastereoselectivity through an exo transition state. Oppolzer's chiral auxiliary was utilized to access an enantiopure cyclic amino acid by this approach, which will enable future biological applications.
authors.affiliation: Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas , 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, United States.
authors.forename: Aaron
authors.initials: A
authors.lastname: Nash
authors.forename: Arash
authors.initials: A
authors.lastname: Soheili
authors.forename: Uttam K
authors.initials: UK
authors.lastname: Tambar
mesh_terms: D000586:Amination; D000598:Amino Acids, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000598:Amino Acids, Cyclic; D010165:Palladium; D012428:Ruthenium; D005998:Glycine