Single Step Conversion of Chiral Carnitine and Derivatives into (S)- and (R)-β-Substituted-γ-Butyrolactones

Giuseppina Calvisi; Roberto Catini; Wilma Chiariotti; Fabio Giannessi; Sandra Muck; Maria Ornella Tinti; Francesco De Angelis

doi:10.1055/s-1997-686

Synlett 1997; 1997(1): 71-74
DOI: 10.1055/s-1997-686

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Single Step Conversion of Chiral Carnitine and Derivatives into (S)- and (R)-β-Substituted-γ-Butyrolactones

Giuseppina Calvisi, Roberto Catini, Wilma Chiariotti, Fabio Giannessi¹ , Sandra Muck, Maria Ornella Tinti, Francesco De Angelis²

¹Dipartimento Ricerca Chimica, Sigma-Tau, Via Pontina Km 30.400, I-00040 Pomezia, Roma, Italy, Fax No. +39.6.91393638
²Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università di L’Aquila, Via Assergi 6, I-67100 L’Aquila, Italy

Abstract

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This paper describes an efficient single step transformation of chiral carnitine and carnitine derivatives into stereoisomerically pure (S)- and (R)-β-substituted-γ-butyrolactones, obtained by intramolecular nucleophilic displacement. (S)- Or (R)-carnitine and (R)-aminocarnitine inner salts give β-hydroxy-γ-butyrolactone and β-amino-γ-butyrolactone respectively (82% and 77%) with the same configuration as the starting material. (R)-Acetylaminocarnitine inner salt gives (R)-β-acetylamino-γ-butyrolactone (90%), while (R)-acetylcarnitine gives 2(5H)-furanone under the same reaction conditions (77%, via cyclization and subsequent elimination reaction). (R)-N-Benzyloxycarnitineamide gives a mixture of pyrrolidinone (11%) and furanoyl imidate (50%) derivatives. The direct transformation of wast (S)-carnitine into the valuable (S)-β-hydroxy-γ-butyrolactone or (after acetylation) into the precious 2(5H)-furanone is of particular interest.

carnitine (S)-β-hydroxy-γ-butyrolactone - aminocarnitine - (R)-β-amino-γ-butyrolactone - 2(5H)-furanone

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