Synthesis of 5S-(1-oxoalkyl and aryl)2-pyrrolidinone derivatives

Article abstract of DOI:10.1080/00397919808006869

N-Benzyl pyroglutamate esters react with aryllithium reagents and methyllithium to give moderate to good yields of 5-(I-oxoaryl) or 5-(I- oxoalkyl)-2-pyrrolidinone derivatives. The reaction proceeds without racemization, but is accompanied by formation of 5-(I-hydroxy- l-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.

Full text of DOI:10.1080/00397919808006869

Synthetic Communications
ISSN: 0039-7911 (Print) 1532-2432 (Online) Journal homepage: http://www.tandfonline.com/loi/lsyc20
Synthesis of 5S-(1-Oxoalkyl and Aryl)-2-
pyrrolidinone Derivatives1
Jeffrey Deskus , Dongping Fan & Michael B. Smith
To cite this article: Jeffrey Deskus , Dongping Fan & Michael B. Smith (1998) Synthesis of 5S-(1-
Oxoalkyl and Aryl)-2-pyrrolidinone Derivatives1 , Synthetic Communications, 28:9, 1649-1659,
DOI: 10.1080/00397919808006869
To link to this article: http://dx.doi.org/10.1080/00397919808006869
Published online: 22 Aug 2006.
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Date: 22 February 2016, At: 12:26