Citation: He Yicheng, Pi Chao, Wu Yangjie, Cui Xiuling. Ring opening [3+2] cyclization of azaoxyallyl cations with benzo[d]isoxazoles: Efficient access to 2-hydroxyaryloxazolines[J]. Chinese Chemical Letters, ;2020, 31(2): 396-400. doi: 10.1016/j.cclet.2019.09.025 shu

Ring opening [3+2] cyclization of azaoxyallyl cations with benzo[d]isoxazoles: Efficient access to 2-hydroxyaryloxazolines

Department of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, China

pichao@zzu.edu.cn

cuixl@hqu.edu.cn

Received Date: 22 July 2019
Revised Date: 7 September 2019
Accepted Date: 12 September 2019
Available Online: 13 September 2019

Figures(5)

A selective ring-opening [3+2] cyclization reaction of benzo[d]isoxazoles with 2-bromo-propanamides has been developed. The azaoxyallyl cation intermediates are employed as C~O 3-atom synthon to build oxa-heterocycles via the selectivity of suitable cyclization partners. This transformation provides rapid access to highly functionalized 2-hydroxyaryl-oxazolines under mild conditions and excellent regioselectivity.
- Azaoxyallylic cations,
- Ring-opening,
- [3+2] Cycloaddition,
- 2-Hydroxyaryl-oxazolines,
- C~O 3-atom synthon
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