Asymmetric Addition Reactions of Organozinc to Aldehydes and Ketones by β-Amino Thiol (-)-MITS

99

This thesis reports the application of β-amino thiol (-)-MITS, prepared from (+)-camphorsulfonic acid, in catalytic asymmetric addition reactions of arylzincs to carbonyl group. Using 5mol% of (-)-MITS for the addition of phenylzinc to aldehydes to construct (R)-diarylmethanol with high yields (up to 99%) and ee values (up to 96%). The addition of aryllzincs to benzaldehyde afforded (S)-diarylmethanol with high yields (up to 99%) and ee values (up to 86%). Treatment of arylethanones with phenylzinc in the presence of 10 mol% (-)-MITS afforded (R)-diarylethanol with up to 51% yields and up to 79% ee.