Enantioselective Iridium-Catalyzed
Allylic Aminations of Allylic Carbonates with Functionalized Side
Chains. Asymmetric Total Synthesis of (S)-Vigabatrin

Christian Gnamm; Géraldine Franck; Nicole Miller; Timon Stork; Kerstin Brödner; Günter Helmchen

doi:10.1055/s-0028-1083158

FEATUREARTICLE

Enantioselective Iridium-Catalyzed Allylic Aminations of Allylic Carbonates with Functionalized Side Chains. Asymmetric Total Synthesis of (S)-Vigabatrin

Christian Gnamm, Géraldine Franck, Nicole Miller, Timon Stork, Kerstin Brödner, Günter Helmchen*
Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
Fax: +49(6221)544205 ; e-Mail: g.helmchen@oci.uni-heidelberg.de ;

Abstract

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Abstract

Iridium-catalyzed aminations of allylic carbonates containing a variety of O-functional groups have been explored. High degrees of regio- as well as enantioselectivity were achieved with diacylamides under salt-free conditions and with arylamines. The results allowed the antiepilepsy drug (S)-vigabatrin to be prepared via a very short route.

Key words

aminations - iridium - asymmetric catalysis - nucleophiles - regioselectivity

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References

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