One-pot synthesis of enantiomerically pure (methylenecyclopropyl)carbinol : a key intermediate to the synthesis of the causative agent of Jamaican vomiting sickness

Enantiomerically pure (R)- and (S)-(methylenecyclopropyl)carbinol was synthesized in a one-pot operation by the reaction of methylenetriphenylphosphane with (R)- and (S)-epichlorohydrin followed by the addition of paraformaldehyde (23 and 18% yield). The yields of this compound were improved by the following two-step reaction. The reaction of methylenetriphenylphosphorane with epichlorohydrin afforded the corresponding (3,4-epoxybutyl)triphenylphosphonium iodide in 83% yield. This phosphonium salt further reacted with NaH followed by the addition of paraformaldehyde to give enantiomerically pure (methylenecyclopropyl)carbinol in 71% yield. The present method affords the short-step synthesis of (methylenecyclopropyl)carbinol compared with the known methods