Synthesis of a cyclic chiral axially disymmetric tetramethylethylenediamine-like but non chelating 1,2-diamine

Abstract

The diamine (S)-(3), obtained by treatment of (S)-1,1′-binaphthyl-2,2′-dicarboxylic acid chloride with N,N′-dimethylethylene-1,2-diamine, is evaluated as a chiral catalyst for addition of n-butyl-lithium to benzaldehyde, but leads to racemic 1-phenylpentan-1-ol, which is interpreted as a failure to complex the BuⁿLi.