Chemoenzymatic routes to cyclopentenols: the role of protecting groups on stereo- and enantioselectivity

Both (R)- and (S)-4-triisopropylsilyloxycyclopent-2-en-1-ones were prepared in enantiopure form in high yields (37-64%) from (±)-4-hydroxycyclopent-2-en-1-one, itself easily obtained from furfuryl alcohol. The chirality was introduced from either enzymatic resolution or desymmetrization. TIPS proved to be the best protecting group.