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Synfacts 2007(11): 1200-1200  
DOI: 10.1055/s-2007-991234
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

In(OTf)3-Promoted Addition of Diethyl Acetamidomalonate to Terminal Alkynes

Contributor(s): Paul Knochel, Andrei Gavryushin
P. Angell, G. Blazecka, M. Lovdahl, J. Zhang*
Pfizer, Inc., Ann Arbor, USA
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Publikationsdatum:
23. Oktober 2007 (online)

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Significance

This publication describes an interesting method for the Markovnikov addition of a carbon nucleophile to a triple bond, catalyzed by In(III). It gives a simple access to non-natural unsaturated and β-branched α-amino acids of high utility for the synthesis of new drug candidates, starting from simple precursors. The method has also a good potential for the development of an enantioselective preparation of non-natural α-amino acids, using asymmetric hydrogenation methods.