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

Giuseppe Bartoli; Marcella Bosco; Enrico Marcantoni; Massimo Massaccesi; Samuele Rinaldi; Letizia Sambri

doi:10.1055/s-2004-829192

PSP

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

Giuseppe Bartoli*^a, Marcella Bosco^a, Enrico Marcantoni^b, Massimo Massaccesi^a, Samuele Rinaldi^c, Letizia Sambri^a
^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

Abstract

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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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References

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17a

This procedure can be successfully applied, with slight modifications (the use of BH₃·py complex instead of BH₃·Me₂S) to closely related systems.

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