Highly Diastereoselective Ring-Opening Reactions of Chiral Acetals with Secondary or Sterically Hindered Grignard Reagents

Article abstract of DOI:10.1021/jo00105a041

1,4-Di-tert-alkoxy-(2S,3S)-2,3-butanediols 2 were obtained from the reactions of 2S,3S-threitol bisketals with Grignard reagents.The reactions of benzylic acetals 3, prepared from 1,4-di-tert-alkoxy-(2S,3S)-2,3-butanediols and aromatic aldehydes, with aryl or secondary or sterically hindered Grignard reagents give the corresponding ring-opening products 4 in high diastereoselectivity.