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Synthesis 2002(10): 1365-1372
DOI: 10.1055/s-2002-33121
DOI: 10.1055/s-2002-33121
PAPER
© Georg Thieme Verlag Stuttgart · New York
Efficient Synthesis of Diastereomerically Pure 1,3-Diamines
Further Information
Received
11 October 2001
Publication Date:
01 August 2002 (online)
Publication History
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