SYNTHESIS AND STEREOCHEMISTRY OF L-2-ALKYL-1,2,3,4-TETRAHYDROQUINOLINE-3,4-EPOXIDES

Analogous to the recently described synthesis of Reissert epoxides the treatment of 1-acyl-2-alkyl-1,2-dihydroquinolines with m-chloroperoxy benzoic acid gave diasteromeric pure epoxides which are stable in crys talline state, but reactive in solution versus nucleophiles. Acting as useful intermediates to stereocontrolled functionalized 1,2,3,4-tetra hydroquinolines an X-ray analysis was performed to confirm the relativ e stereochemistry of the epoxides.