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Regio- and Diastereoselective Access to 4‑Imidazolidinones via an Aza-Mannich Initiated Cyclization of Sulfamate-Derived Cyclic Imines with α‑Halo Hydroxamates

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posted on 2019-06-17, 00:00 authored by Jing Zhou, Hong Zhang, Xue-Lian Chen, Ya-Li Qu, Qianqian Zhu, Chen-Guo Feng, Ya-Jing Chen
An efficient regio- and diastereoselective cyclization of sulfamate-derived cyclic imines with unsubstituted or monosubstituted α-halo hydroxamates is developed under mild conditions. This reaction proceeds smoothly under transition-metal-free conditions via a domino aza-Mannich addition/intramolecular nucleophilic substitution sequence, providing a convenient route to access 2-monosubstituted and 2,5-disubstituted 4-imidazolidinones. Notably, the products were obtained with single trans-isomers in moderate to excellent yields.

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