Transformation of (+)-thiomicamine into a new ligand for the enantioselective addition of methyllithium to prochiral imines

A new ligand 2 was prepared from (+)-thiomicamine 1 and o-methoxyphenol, an d its activity as an external controller of stereochemistry in enantioselec tive additions of methyllithium to prochiral imines 8-10 tested. The non-ra cemic secondary amines 11-13 were prepared in 60-90% chemical yield with th e enantioselectivity ranging from 2 to 41%. 6,7-Dimethoxy-3,4-dihydroisoqui noline 8 was transformed into (+)-salsolidine 11 with an e.e. of 41%. (C) 2 000 Elsevier Science Ltd. All rights reserved.