FACILE SYNTHESIS OF OPTICALLY ACTIVE 2-HYDROXYMETHYL-4-METHYLENECYCLOHEXANOL - DE NOVO SYNTHESIS OF DIDEOXYCARBOCYCLIC SUGARS

摘要

Treatment of the olefinic epoxy alcohol 4 with diethylaluminum fluoride gives the hydroxymethyl methylenecyclohexanol 5 in yields of 60-75% rather than the other possible epoxide opening product 6 presumably due to a geometrical constraint similar to that in Baldwin's rules for ring closure. [References: 28]