title: Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid. Preparation of alpha-hydroxy-gamma-amino acid derivatives.
abstract: [reaction--see text] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to alpha,beta-unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives alpha-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to gamma-lactams, which can be easily converted into alpha-hydroxy-gamma-amino acid derivatives.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK. .
authors.forename: D J
authors.initials: DJ
authors.lastname: Dixon
authors.forename: S V
authors.initials: SV
authors.lastname: Ley
authors.forename: F
authors.initials: F
authors.lastname: Rodríguez
mesh_terms: D000080:Acetals; D002384:Catalysis; D007202:Indicators and Reagents; D008094:Lithium; D018020:Lithium Compounds; D009682:Magnetic Resonance Spectroscopy; D012821:Silanes
chemical_list: D000080:Acetals; D007202:Indicators and Reagents; D018020:Lithium Compounds; D012821:Silanes; C442342:butane-2,3-diacetal glycolic acid; D008094:Lithium; C442341:lithium hexamethyldisilazide