Resurrecting the Cornforth Model for Carbonyl Addition: Studies on the Origin of 1,2-Asymmetric Induction in Enolate Additions to Heteroatom-Substituted Aldehydes


  • Financial support was provided by the National Institutes of Health (GM33327-16) and by Merck Research Laboratories.


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Further experimental support for the Cornforth model is obtained from a systematic study of aldol reactions between methyl-substituted E and Z enolates and α-oxygen-substituted aldehydes. The observed dependence of diastereofacial selectivity on enolate configuration in this case is more consistent with the Cornforth model than with the the polar Felkin–Anh model (see scheme; X=OR, NR2, Cl).