Highly enantioselective rearrangement of a meso-epoxide to an allyl alcohol for carbocyclic nucleoside synthesis: An internal alkoxide effect

Hodgson DM, Witherington J, Moloney BA

The synthesis of the enantiomeric cis-4-(hydroxymethyl)cyclopent-2-ene-1-ols 2 and 3 (R = H) via a highly enantioselective rearrangement of cis-6-oxabicyclo[3.1.0]hexane-3-methanol 4 (R = H) using the dilithium salts of(+)- or (-)-norephedrine is described. © 1994.