Abstract

The synthesis of syn-2,4-dimethyl-1-tetralone 6 via a reprotonation strategy using chelating proton donors is discussed. We comment on the comformational effects associated with these acids, and discuss the differences between direct protonation and deprotonation-reprotonation of chiral enolates in the presence of diisopropylamine and LiBr.Key words: conformation, chelating proton donors, deprotonation-reprotonation strategy, diastereoselective protonation and solvent effects.

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