Carbenoid insertions into the siliconhydrogen bond catalyzed by chiral copper (I) schiff base complexes

Abstract

An asymmetric insertion reaction of α-diazoesters derived from methyl arylacetates into the silicon-hydrogen bond of silanes was achieved using a copper (I) catalyst associated with a chiral, C 2 symmetric Schiff base. Addition of the diazoesters 1 (1 equiv) to the Cu·Lig complex (R,R)- 3 (0.1 equiv) in the presence of the silane reagent (1.5 equiv) at −40° C yielded the corresponding insertion products 2 or 4 in good yields with varying levels of selectivity (up to 84% ee).