Local conformer effects in unsaturated lactones

…, WH Dent III, DM Gapinski, CK McClure

Index: Vedejs, E.; Dent, W. H.; Gapinski, D. M.; McClure C. K. Journal of the American Chemical Society, 1987 , vol. 109, # 18 p. 5437 - 5446

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Citation Number: 47

Abstract

Abstract: Allylic unsaturated lactones 5E and 5Z can be epoxidized and osmylated with useful stereocontrol. The epoxidations follow the pattern predicted from evaluation of local conformer effects, and epoxides 8 and 14 are favored. These products correspond to peripheral attack on the exposed olefin face of conformers similar to 1 (Z-alkene) or 2 (E- alkene). As in the case of simple carbocyclic alkenes, osmylation of the Z-isomer (5Z) ...