Facile synthesis of optically active 2-hydroxymethyl-4-methylenecyclohexanol. De novo synthesis of dideoxycarbocyclic sugars

Article abstract of DOI:10.1016/0040-4039(95)02067-5

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.