Synthesis of 5,5′-Disubstituted Bimorpholines

Abstract

A general method for the synthesis of 5,5′-disubstituted bimorpholines is proposed. According to the method, methyl-substituted and benzyl-substituted compounds were synthesized, starting from tartaric ester acetal. Target compounds were obtained in good yield and high enantiomeric purity.

Keywords:

• Asymmetric synthesis
• bimorpholine
• cyclic diamines

ACKNOWLEDGMENTS

The authors thank the Estonian Science Foundation (Grant Nos. 6662 and 6778), the Ministry of Education and Research (Grant No. 0142725S06), and EU European Regional Development Fund (3.2.0101.08–0017) for financial support. The authors are grateful to Lauri Peil (Ph.D.), University of Tartu, Institute of Technology proteomics core facility, for HRMS analysis.

Notes

^a Not determined.

^b No reaction.

^c Microwave reactor CEM Discover-S.