Diamine Ligands for Asymmetric Catalysis: Facile Synthesis of C2-Symmetric Piperazines from Seebach’s Oxazolidinone

Zbigniew Kałuża; Rafał Ćwiek; Mirosław Dygas; Przemysław Kalicki

doi:10.1055/s-0034-1378341

Synlett, Table of Contents

Synlett 2014; 25(13): 1883-1887
DOI: 10.1055/s-0034-1378341

letter

Diamine Ligands for Asymmetric Catalysis: Facile Synthesis of C₂-Symmetric Piperazines from Seebach’s Oxazolidinone

Zbigniew Kałuża*

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 Email: zbigniew.kaluza@icho.edu.pl

,

Rafał Ćwiek

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 Email: zbigniew.kaluza@icho.edu.pl

,

Mirosław Dygas

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 Email: zbigniew.kaluza@icho.edu.pl

,

Przemysław Kalicki

Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 Email: zbigniew.kaluza@icho.edu.pl

› Author Affiliations

Abstract

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Dedicated to Professor Mieczysław Mąkosza on the occasion of his 80^th birthday

Abstract

C₂-Symmetrical hemiaminal ethers and diamines with a piperazine core were synthesized starting from Seebach’s oxazolidinone. The new methodology is based on the dimerization of α-amino aldehydes to bicyclic bishemiaminal ethers, followed by reduction to the corresponding diamines. Several enantiopure piperazine derivatives bearing either methyl or bulky groups including isopropyl and aryl at the bridgehead carbon atoms were obtained applying this methodology. Initial screening of new ligands in the copper-catalyzed asymmetric acylation of meso-1,2-diols produced promising results (up to 92% ee).

Key words

asymmetric synthesis - catalysis - diamine ligands

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References

References and Notes

For comprehensive reviews, see:

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