Enantioselective catalytic lithiation using a chiral binaphthyl derivative as electron carrier

The lithiation, of the secondary chloride 2, catalyzed by binaphthyl derivatives, i.e. BINAM 4, BINOL 5, BINAP 6, H8-BINAP 7, Tol-BINAP 8, 2,2’-bis(pyrrolidin-1-yl)-1,1’-binaphthalene 9, and 2,2’-dimethyl-1,1’-binaphthalene 11, in the presence of different ketones has been studied, yielding the corresponding alcohol derivatives 3 and 12-16 in moderate to good yields. Binaphthyl derivative 11 has revealed to be very active as catalyst in the lithiation process at room temperature, and has allowed the preparation of the alcohol derivatives with enantioselectivities up to 50%.

Financial support from the Ministerio de Ciencia e Innovación (MICINN) of Spain (Project Nos. CTQ2007-65218, CTQ2011-24165, Consolider Ingenio 2010 CSD2007-00006), the Generalitat Valenciana (PROMETEO/2009/0349 and FEDER), and the Universidad de Alicante is acknowledged.