Amino Acid-Derived trans- N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility.

Amer, Mostafa Mahmoud; Abas, Hossay; Leonard, Daniel J; Ward, John W; Clayden, Jonathan

Amer, Mostafa Mahmoud; Abas, Hossay; Leonard, Daniel J; Ward, John W; Clayden, Jonathan.

Afiliación

Amer MM; School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Abas H; School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Leonard DJ; School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Ward JW; School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Clayden J; School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.

J Org Chem ; 84(11): 7199-7206, 2019 06 07.

Article en En | MEDLINE | ID: mdl-31090419

RESUMEN

N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by "self-regeneration of stereochemistry" methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presence of pyridine may be made fully diastereoselective for the trans-N-chloroformylimidazolidinones, and we detail the conformational features of the products. We show that despite the presence of the electrophilic carbamoyl chloride function the products show remarkable stability and may be deprotonated to form enolates with useful reactivity for the synthesis of amino acid derivatives.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos

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