title: Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives.
abstract: The camphor-derived tetrahydropyran (camTHP*)-desymmetrized glycinamide 1 undergoes efficient and highly diastereoselective lithium enolate Michael additions to nitro olefins, alpha,beta-unsaturated ketones, esters, and lactones. Straightforward manipulation of these products affords 3-substituted pyroglutamides and beta-aryl-alpha,gamma-diamino acid derivatives, highlighting the ease of synthesis of enantiomerically enriched, functionally dense molecules using this novel building block. [reaction: see text]
authors.affiliation: Department of Chemistry, University of Manchester, Manchester, M13 9PL, U.K. darren.dixon@man.ac.uk
authors.forename: Darren J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: Richard A J
authors.initials: RA
authors.lastname: Horan
authors.forename: Nathaniel J T
authors.initials: NJ
authors.lastname: Monck
authors.forename: Paul
authors.initials: P
authors.lastname: Berg
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis*; D002164:Camphor / Q000737:chemistry; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; C018556:glycine amide; D002164:Camphor; D005998:Glycine