title: N-alkyl oxazolidines as stereocontrol elements in asymmetric Diels-Alder cycloadditions of 9-substituted anthracene derivatives.
abstract: Chiral 9-oxazolidinyl anthracene derivatives have been prepared as single diastereoisomers by condensation of 9-anthraldehyde with the appropriate N-alkyl amino alcohol. Asymmetric Diels-Alder cycloadditions of these with N-methyl maleimide proceeds in good yield and in good diastereoselectivity, the sense of which may be controlled by judicious choice of the N-alkyl group.
authors.affiliation: Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, UK.
authors.forename: Harry
authors.initials: H
authors.lastname: Adams
authors.forename: Ramadan A
authors.initials: RA
authors.lastname: Bawa
authors.forename: Simon
authors.initials: S
authors.lastname: Jones
mesh_terms: D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D012680:Sensitivity and Specificity; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: D000873:Anthracenes; D010080:Oxazoles; C034020:anthracene