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Synthesis 2002(10): 1365-1372
DOI: 10.1055/s-2002-33121
PAPER
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Diastereomerically Pure 1,3-Diamines

Beatrix Merla, Nikolaus Risch*
Fachbereich Chemie und Chemietechnik, Universität Paderborn, Warburger Str. 100, 33098 Paderborn, Germany
Fax: +49(5251)603245; e-Mail: nr@chemie.uni-paderborn.de;
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Publication History

Received 11 October 2001
Publication Date:
01 August 2002 (online)

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Abstract

The regio- and diastereoselective synthesis of 1,3-diamines using inexpensive starting materials is described. β-­Aminoketones are easily transformed diastereoselectively into syn, anti-, anti, anti-, or anti, syn-1,3-diamines using different methodologies. The configuration of the products was determined by NMR.

Key words

diastereoselectivity - reductions - regioselectivity - Schiff bases - stereoselectivity

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In one case the deprotection of compound 4 with R′ = Bn was not possible within a reasonable time: R1 = Ph, R2 = Me, R′ = Bn, NR4 2 = N(CH2)4O