Abstract
The enantioselectivity of the intramolecular asymmetric aldol reaction mediated by (S)-2-(pyrrolidinylmethyl)pyrrolidine to prepare Wieland-Miescher ketone was examined in detail. A remarkable inversion of enantioselectivity was observed when a Bronsted acid was used as a co-catalyst. Development of the reaction to Robinson annulation was successfully achieved by the use of (S)-2-(pyrrolidinylmethyl)pyrrolidine as a Bronsted base, followed by trifluoroacetic acid as a Bronsted acid.
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