A Convenient Conversion of α-Aminoacids into NH-Boc Protected α-Aminoketones via Imidazolides

Bianca F. Bonini; Mauro Comes-Franchini; Mariafrancesca Fochi; Germana Mazzanti; Alfredo Ricci; Greta Varchi

doi:10.1055/s-1998-1831

Synlett 1998; 1998(9): 1013-1015
DOI: 10.1055/s-1998-1831

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A Convenient Conversion of α-Aminoacids into NH-Boc Protected α-Aminoketones via Imidazolides

Bianca F. Bonini^* , Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci, Greta Varchi

^*Dipartimento di Chimica Organica "A. Mangini", Università di Bologna, Viale Risorgimento 4, I-40124-Bologna (Italy); Fax + 39 51 6 44 36 54; E-mail: ricci@ms.fci.unibo.it

Abstract

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Imidazolides obtained from natural α-aminoacids react with a twofold excess of Grignard reagents to afford in satisfactory to good yields the corresponding NH-Boc protected α-aminoketones. Under optimized conditions the reaction with phenyl- and n-pentylmagnesium bromide required the addition of catalytic amounts of Cu(I)-salt which turned out to be unnecessary in the case of Buchi's Grignard.

α-aminoacids - imidazolides - Grignard reagents - Cu(I)-catalysis - α-aminoketones

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