Enantioselective Deprotonation of Cyclohexene Oxide to (R)-2-Cyclohexen-1-ol

Abstract

The reaction of cyclohexene oxide with homochiral lithium amides, prepared from (S)-phenylglycine and (S)-valine has been studied and (R)-2-cyclohexen-1-ol 3 was prepared in a maximum of 72% ee. The optical purity was determined by ¹H NMR measurement of the α-methoxy-α-(trifluoromethyl)phenyl acetic acid (MTPA) derivative of the corresponding alcohol.