Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines:: switchover of diastereofacial selectivity

Diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines gave alkylated adducts in high yields and diastereoselectivities. Cleavage of the chiral auxiliary under mildly acidic conditions gave diarylmethylamines in high yield. A reversal in the diastereoselectivity was observed by using either phenylmagnesium bromide in toluene or phenyllithium in THF. The use of the same chiral auxiliary thus allowed the synthesis of both enantiomers of a number of diarylmethylamines. (C) 2002 Elsevier Science Ltd. All rights reserved.