Experimental study demonstrates enantioselective alpha-methylation in chiral amides, suggesting chirality transfer within mixed aggregates drives asymmetric induction.
Chiral amides derived from O-methyl mandelic acid and achiral amines underwent enantioselective alpha-methylation on treatment with LTMP followed by addition of methyl iodide; chirality transfer from an undeprotonated chiral amide into an achiral enolate in a mixed aggregate is supposed to be responsible for the asymmetric induction.
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Kawabata et al. (2002) studied this question.
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