PAPER	Synthesis 2005: 2234-2238   DOI: 10.1055/s-2005-869952
© Georg Thieme Verlag Stuttgart · New York
Rhodium-Catalyzed Synthesis of α-Amido- and α-Carboxylic-β-Ketoesters
Søren Bertelsen, Martin Nielsen, Stephan Bachmann, Karl Anker Jørgensen*
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark e-Mail: kaj@chem.au.dk;
Received 20 February 2005

Abstract

The rhodium-catalyzed N-H and O-H insertion of amides and carboxylic acids with α-diazo-β-ketoesters to give different α-amido- and α-carboxylic-β-ketoesters is presented. Investigations were carried out to establish an efficient N-H and O-H insertion reaction using a range of different amides and carboxylic acids for the synthesis of intermediates e.g. for receptor antagonists. The reactions were performed under mild conditions with 1 mol% of catalyst and the products were formed in good yields.

Keywords

amides - carboxylic acids - catalysis - diazo compounds - insertions - rhodium