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