Diastereotopy in some 3,4-dihydroisocoumarins - effect of changing the substituents on the chiral centre

Diastereotopy has been investigated in eight different derivatives of 3,4-dihydroisocoumarins by changing the substituent on the pyran ring chiral centre, C-3. A diastereotopic NMR effect is observed for the prochiral methylene protons on the benzopyran ring and the effect is greatly influenced by the pi-electron system of the substituent. The effect is also observed for the substituents, however, the extent of diastereotopy depends upon their nature and the separation of methylene groups from the chiral centre. (C) 2000 Elsevier Science B.V. All rights reserved.