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Synthesis 2004(18): 3092-3096  
DOI: 10.1055/s-2004-829192
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© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective Synthesis of β-Hydroxy Amides from β-Keto Amides

Giuseppe Bartoli*a, Marcella Boscoa, Enrico Marcantonib, Massimo Massaccesia, Samuele Rinaldic, Letizia Sambria
a Dipartimento di Chimica Organica ‘A. Mangini’, v. le Risorgimento 4, 40136 Bologna, Italy
Fax: +39(51)2093654; e-Mail: giuseppe.bartoli@unibo.it;
b Dipartimento di Scienze Chimiche, Università di Camerino, v. S. Agostino 1, 62032 Camerino (MC), Italy
c Dipartimento di Scienze e Materiali della Terra, Università di Ancona, v. Brecce Bianche, 60131 Ancona, Italy
Further Information

Publication History

Received 1 June 2004
Publication Date:
13 August 2004 (online)

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Abstract

β-Hydroxy amides with stereodefined geometry represent an important unit present in various natural products. The diastereoselective preparation of amides carrying a secondary or tertiary alcohol in β-position is described here.

Key words

diastereoselectivity - hydroxy amides - TiCl4 - organocerium reagents - boranes

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