Synthesis of 5S-(1-Oxoalkyl and Aryl)-2-pyrrolidinone Derivatives1 |
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Authors: | Jeffrey Deskus Dongping Fan Michael B Smith |
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Institution: | Room 151, 215 Glenbrook Road, Department of Chemistry , University of Connecticut , Storrs, Connecticut , 06269-3060 |
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Abstract: | N-Benzyl pyroglutamate esters react with aryllithium reagents and methyllithium to give moderate to good yields of 5-(1-oxoaryl) or 5-(1-oxoalkyl)-2-pyrrolidinone derivatives. The reaction proceeds without racemization, but is accompanied by formation of 5-(1-hydroxy-1-alkyl)-2-pyrrolidinone derivatives. This reaction gives very poor yields of ketone products with most other alkyl organolithium reagents such as n-butyllithium. Grignard reagents react to give primarily the alcohol. |
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