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Issue 40, 2018
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Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

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Abstract

Chiral exocylic vicinal diamines are biologically and chemically important compounds, but they are not easy to make. In this paper, an interesting aminative Umpolung cyclization process has been developed. Aromatic aldehydes 6 bearing an electrophilic chiral sulfinimine group underwent imine formation with 2,2-diphenylglycine (2), decarboxylation, and subsequent Umpolung cyclization, producing various trans-diamines 10 in 84–96% yields with high trans/cis ratios under very mild conditions. This work not only provides an efficient, clean, and mild method for the synthesis of chiral exocyclic vicinal diamines in one step but also represents a new application of aminative Umpolung strategy on intramolecular reactions.

Graphical abstract: Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

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Supplementary files

Article information


Submitted
15 Aug 2018
Accepted
26 Sep 2018
First published
26 Sep 2018

Org. Biomol. Chem., 2018,16, 7498-7502
Article type
Paper

Aminative Umpolung cyclization for synthesis of chiral exocyclic vicinal diamines

F. Liu, G. Zhao, W. Cai, D. Xu and B. Zhao, Org. Biomol. Chem., 2018, 16, 7498
DOI: 10.1039/C8OB02000K

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