N-alkyl oxazolidines as stereocontrol elements in asymmetric Diels-Alder cycloadditions of 9-substituted anthracene derivatives.
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.
Adams
Harry
H
Department of Chemistry, University of Sheffield, Dainton Building, Brook Hill, Sheffield, UK.
Bawa
Ramadan A
RA
Jones
Simon
S
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
D000873:Anthracenes; D010080:Oxazoles; C034020:anthracene