Tetrahedron p. 7521 - 7534 (1994)
Update date:2022-08-03
Topics:
Davies, Stephen G.
Evans, Gary B.
Pearce, Susan
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.
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