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S‐Cinnamyl thiocarbamate 9, easily accessible from cinnamyl alcohol, undergoes smooth deprotonation with n‐BuLi in the presence of various chiral ligands to form configurationally unstable organolithium intemediates. With the proper choice of chiral ligand, the diastereomeric equilibrium is almost fully shifted to one side, furnishing highly enantioenriched products after reaction with various electrophiles.
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Sonawane et al. (2006) studied this question.
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