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Abstract
Abstract The relative magnitude of steric bulk of saturated vs. unsaturated substituents in the title compounds has been estimated by a lanthanoid induced shift (LIS) study of these (R)-(+)-α-methoxy-α-(trifluoromethyl)phenylacetate esters [(R)-(+)-MTPA esters] by 1H NMR spectroscopy: CH2=C(Me)−>Pentyl>n−Pr>Et\simeqCH2=CH−>Me>CH≡C−;Ph>Cyclohexyl These results allow the assignment of the absolute configurations of both cyclic and acyclic unsaturated alcohols. Furthermore, the relative intensity of well-separated OMe signals for those diastereomeric MTPA esters can be used for the determination of the %ee of the original alcohols.
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