157241-86-6Relevant articles and documents
Bifunctional Chiral Auxiliaries 8: Utilisation of Tartaric Acid Derived Auxiliaries in Aldol and Alkylation Reactions
Davies, Stephen G.,Evans, Gary B.,Pearce, Susan
, p. 7521 - 7534 (1994)
The boron enolates of three new homochiral C2 symmetric 1,3-diacylimidazolidin-2-ones prepared from natural tartaric acid undergo highly diastereoselective aldol and alkylation reactions.Cleavage of these diastereomerically pure, adducts gives homochiral (1R,2S)-1-phenyl-2-methylpropane-1,3-diol and (2R,3R)-3-hydroxy-3-phenyl-2-methylpropanoic acid and (2S)-3-phenyl-2-methylpropan-1-ol (>92percent ee.).One of these auxiliaries, 4,5-dimethylimidazolidin-2-one, has the lowest effective molecular weight of any previously reported chiral auxiliary.