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Synthesis of Highly Substituted Imidazolidine-2,4-dione (Hydantoin) through Tf2O-Mediated Dual Activation of Boc-Protected Dipeptidyl Compounds

Hui Liu, Zhimin Yang and Zhengying Pan*

*Laboratory of Chemical Genomics, Laboratory of Structural Biology, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen 518055, China, Email: panzypkusz.edu.cn

H. Liu, Z. Yang, Z. Pan, Org. Lett., 2014, 16, 5902-5905.

DOI: 10.1021/ol502900j (free Supporting Information)


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Abstract

The synthesis of highly substituted chiral hydantoins from simple dipeptides proceeded through the dual activation of an amide and a tert-butyloxycarbonyl (Boc) protecting group by Tf2O-pyridine under mild conditions in a single step. This method was successfully applied in the preparation of various biologically active compounds, including drug analogs and natural products.

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Key Words

Hydantoins


ID: J54-Y2014