Bifunctional chiral auxiliaries 4: Alkylation of enolates derived from 1,3-diacyl-trans-4,5-tetramethyleneimidazolidin-2-ones

Article abstract of DOI:10.1016/S0040-4039(00)91875-6

Addition of alkyl halides to sodium and potassium enolates of 1,3-diacyl-trans-4,5-tetramethyleneimidazolidin-2-ones allows diastereoselective alkylation of both acyl sidechains with the latter enolates showing generally higher stereoselectivities. S-(-)-3-Phenyl-2-methylpropan-1-ol 6 was prepared in this way with a 93% enantiomeric excess.