Synlett 2003(2): 0211-0214
DOI: 10.1055/s-2003-36799
LETTER
© Georg Thieme Verlag Stuttgart · New York

A First Asymmetric Diamination of Olefins

Kilian Muñiz*a, Martin Niegerb
a Kekulé-Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Fax: +49(228)735813; e-Mail: kilian.muniz@uni-bonn.de;
b Institut für Anorganische Chemie, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Further Information

Publication History

Received 13 November 2002
Publication Date:
22 January 2003 (online)

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Abstract

An asymmetric diamination of olefins employing stable imidoosmium(VIII) complexes is described for the first time. The reaction is based on the use of chiral acrylic esters and related substrates with enantiopure menthol and 8-phenyl menthol as chiral auxiliaries and gives rise to osmaimidazolidines with good to excellent diastereomeric ratios (up to 95:5). Removal of the osmium centre and the chiral auxiliary leads to novel enantiopure 1,2,3-trisubstituted compounds.