Divergent synthesis of pyrrolidine and glutamic acid derivatives using a macrocyclic phase-transfer catalyst under high-pressure conditions

Abstract

The reactivity of the glycine ketimine ester with α,β-unsaturated ketones in the presence of macrocyclic hybrid phase-transfer catalysts under high pressure conditions has been investigated. Control during reactions, obtained through the appropriate selection of conditions and specific orientation of hydrogen bond donors located in macrocyclic phase-transfer catalysts, allows obtaining Michael addition or 1,3-dipolar cycloaddition products with a high yield of up to 99% and excellent diastereoselectivity of up to >99 : 1.