Synthesis and Absolute Configuration of (S,S)-[o-(1-Dimethylaminoethyl)phenyl]-phenyl(3,4-dimethoxyphenyl)carbinol

摘要

Previously, we reported on the influence of seric factors on the stereochemistry of the condensation of ortho-lithiated (S,S)-N,N-dimethyl-1-phenylethylamine (I) with asymmetric ketones [1, 2]. For the reaction of I with di- and trimethylbenzophenones, the following assumptions were made concerning the influence of electronic factors: first, the positive inductive effect of two or three methyl groups decreases the reactivity of the carbonyl carbon atom, i.e., it can increase the selectivity of the reaction, and second, it increases the electrondensity in the benzene ring, which prevents two substituted benzene rings (those of amine and benzophenone) from approaching each other.