Chiral ligands containing heteroatoms .14. 1,3-oxazolidinyl methanols as chiral catalysts in the enantioselective addition of diethylzinc to aldehydes

Starting from L-serine and L-threonine, (S)-diphenyl-(2,2-dimethyl-1,3-oxazolidin-4-yl)-methanol and (4S,5R)-diphenyl-(2,2-dimethyl-5-methyl-1,3-oxazolidin-4-yl)-methanol were prepared in good yields. The use of these compounds as very efficient chiral catalysts for the enantioselective addition of diethylzinc to aldehydes is described. This paper reports the first example of the use of oxazolidine methanols in asymmetric synthesis.