α-Quaternary Proline Derivatives by Intramolecular Diastereoselective Arylation of N-Carboxamido Proline Ester Enolates

Julien Maury, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

12 Citations (Scopus)

Abstract

Pyrrolidine-2-carboxylate esters substituted in the 3-, 4- or 5-positions were converted to their N′-aryl urea derivatives. Deprotonation at the 2-position to form a potassium enolate led to migration of the N′-aryl substituent to the 2 position of the pyrrolidine ring, followed by cyclization of the resulting urea to give bicyclic α-aryl hydantoin derivatives of substituted prolines. Depending on the substitution pattern of the starting material, high diastereoselectivity was observed in the aryl migration, allowing formation of the products in enantiomerically enriched form, despite the intermediacy of a planar enolate. The hydrolysis of the bicyclic hydantoins under basic conditions gave a range of enantiopure and enantioenriched quaternary α-aryl proline derivatives.

Original languageEnglish
Pages (from-to)10757-10768
Number of pages12
JournalJournal of Organic Chemistry
Volume80
Issue number21
DOIs
Publication statusPublished - 6 Nov 2015

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