Synthesis of enantiomerically and diastereomerically pure cyclopentanols by asymmetric cyclocarbolithiation of 5-alkenyl carbamates

Article abstract of DOI:10.1002/anie.199717641

Three vicinal stereocenters are formed in the (-)-sparteine-induced cyclocarbolithiation of 6-phenyl-5-hexenyl carbamates. The anionic cyclization products can be trapped with various electrophiles (El) to provide enantiomerically pure cyclopentanol derivatives [Eq. (a); Cby = 2,2,4,4-tetramethl-1,3-oxazolidin-3-carboxylate].