CHIRAL NAPHTHAFUROPHANES FROM FURAN MACROCYCLES

The cycloaddition of two moles of benzyne with any two non diametrical ly opposite furan units of 1 in an anti geometry yields a chiral macro cycle. The chiral anti-1,3-bis-adduct 2 has been isolated, characteris ed bg X-ray crystallography, and converted into the corresponding dina phthafuropnane 4. The X-ray analysis of 4 shows the crystals to contai n only a single enantiomer i.e. I undergoes spontaneous resolution on crystallisation. Copyright (C) 1996 Elsevier Science Ltd