Breaking aziridines to construct morpholines with a gold(I)-catalyzed tandem ring-opening and cycloisomerization reaction

Shuyao Zhang; Chuan Shan; Shuai Zhang; Luye Yuan; Jianwu Wang; Chen-Ho Tung; Ling-Bao Xing; Zhenghu Xu

doi:10.1039/C6OB02284G

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Breaking aziridines to construct morpholines with a gold(i)-catalyzed tandem ring-opening and cycloisomerization reaction†

Shuyao Zhang,^a Chuan Shan,^a Shuai Zhang,^a Luye Yuan,^a Jianwu Wang,*^a Chen-Ho Tung,^a Ling-Bao Xing*^a and Zhenghu Xu

*^ab

Author affiliations

* Corresponding authors

^a Key Lab for Colloid and Interface Chemistry of Education Ministry, School of chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
E-mail: xuzh@sdu.edu.cn

^b State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China

Abstract

A convenient synthetic method for the construction of morpholine derivatives from easily available aziridines and propargyl alcohols has been successfully developed. A tandem nucleophilic ring-opening of aziridine/6-exo-dig cyclization/double bond isomerization sequence was achieved by using a single gold(I) catalyst under mild conditions. The gold(I) catalyst served as a π acid and also a σ acid to realize the dual activation of both reactants in this reaction. The obtained unsaturated morpholine products could be easily hydrogenated to achieve target morpholine derivatives with good diastereoselectivities in high yields.

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DOI: https://doi.org/10.1039/C6OB02284G
Article type: Paper
Submitted: 19 Oct 2016
Accepted: 27 Oct 2016
First published: 27 Oct 2016

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Org. Biomol. Chem., 2016,14, 10973-10980

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Breaking aziridines to construct morpholines with a gold(I)-catalyzed tandem ring-opening and cycloisomerization reaction

S. Zhang, C. Shan, S. Zhang, L. Yuan, J. Wang, C. Tung, L. Xing and Z. Xu, Org. Biomol. Chem., 2016, 14, 10973 DOI: 10.1039/C6OB02284G

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Organic & Biomolecular Chemistry

Breaking aziridines to construct morpholines with a gold(i)-catalyzed tandem ring-opening and cycloisomerization reaction†

Abstract

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Breaking aziridines to construct morpholines with a gold(I)-catalyzed tandem ring-opening and cycloisomerization reaction

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