Efficient Synthesis of Diastereomerically Pure 1,3-Diamines

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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22

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