Chiral lithium 2-aminoalkoxides ((1R, 2S)-4) were applied as chiral bases for the enantioselective Horner-Wadsworth-Emmons reaction between achiral phosphonates (2) and 4-tert-butylcyclohexanone (1). A chiral olefin ((R)-3b) was obtained in up to 52% enantiomeric excess (ee). It is shown that the formation of the lithium aldolate intermediate is reversible and is not responsible for the asymmetric induction.
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Kumamoto et al. (1997) studied this question.