Anti-Selective Aldol Reaction of Benzylic Nitriles and Synthesis of γ-Amino Alcohols

Article abstract of DOI:10.1021/jo00128a025

The stereochemistry of the aldol reaction of seven benzylic nitriles 1a-g and four aldehydes 2-5 has been studied.In all cases studied the reaction is anti-selective.Good to excellent selectivity (10:1 -> 20:1) can be obtained if aldehydes with bulky secondary or tertiary substituents are used.The resulting aldols 6-9 are easily transformed to the corresponding γ-amino alcohols 12-15, which may possess useful antidepressant activity.