Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Phosphine Catalyzed Michael-Type Additions: Synthesis of Glutamic Acid Derivatives from Arylidene-α-Amino Esters

Version 1 : Received: 15 December 2023 / Approved: 18 December 2023 / Online: 18 December 2023 (13:14:56 CET)

A peer-reviewed article of this Preprint also exists.

Rodríguez-Flórez, L.V.; González-Marcos, M.; García-Mingüens, E.; Retamosa, M.G.; Kawase, M.; Selva, E.; Sansano, J.M. Phosphine Catalyzed Michael-Type Additions: The Synthesis of Glutamic Acid Derivatives from Arylidene-α-amino Esters. Molecules 2024, 29, 342. Rodríguez-Flórez, L.V.; González-Marcos, M.; García-Mingüens, E.; Retamosa, M.G.; Kawase, M.; Selva, E.; Sansano, J.M. Phosphine Catalyzed Michael-Type Additions: The Synthesis of Glutamic Acid Derivatives from Arylidene-α-amino Esters. Molecules 2024, 29, 342.

Abstract

The reaction of arylidene-α-amino esters with electrophilic alkenes to yield the Michael type addition compounds is optimized using several phosphines as organocatalysts. The transformation is very complicated due to the generation of several final compounds, including those derived from the 1,3-dipolar cycloadditions. For this reason, the selection of the reaction conditions is a very complex task and the slow addition of the acrylic system is very important to complete the reaction. The study of the variation of the structural components of the starting imino ester is performed as well as the expansion of other electron-poor alkenes. The crude products have a purity higher than 90% in most cases without any purification. A plausible mechanism is detailed based on the bibliography and the experimental results. The synthesis of pyroglutamate entities, after reduction of the imino group and cyclization, is performed in high yields. In addition, the hydrolysis of the imino group, under acidic media, represents a direct access to glutamate surrogates.

Keywords

organocatalysis; phosphines; imino esters; Michael addition; glutamates; pyroglutamates

Subject

Chemistry and Materials Science, Organic Chemistry

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