Issue 20, 2021

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
11 avg 2021
Accepted
20 avg 2021
First published
23 avg 2021

Org. Chem. Front., 2021,8, 5888-5894

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

A. Tyszka-Gumkowska and J. Jurczak, Org. Chem. Front., 2021, 8, 5888 DOI: 10.1039/D1QO01198G

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