Direct access to spirobiisoxazoline via the double 1,3-dipolar cycloaddition of nitrile oxide with allenoate†,Organic & Biomolecular Chemistry

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Direct access to spirobiisoxazoline via the double 1,3-dipolar cycloaddition of nitrile oxide with allenoate†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2018-01-04 00:00:00 , DOI: 10.1039/c7ob03040a
Xinye Shang _{1,

2,

3,

4,

5} , Kun Liu _{1,

2,

3,

4,

5} , Zhongyin Zhang _{1,

2,

3,

4,

5} , Xianhong Xu _{1,

2,

3,

4,

5} , Pengfei Li _{5,

6,

7,

8} , Wenjun Li _{1,

2,

3,

4,

5}

Affiliation

The double [3 + 2]-cycloadditions between nitrile oxides and allenoates have been achieved. In the presence of DABCO combined with Et₃N, 2-substituted buta-2,3-dienoates reacted with oxime chlorides to afford spirobiisoxazolines in 55–90% yields via the double 1,3-dipolar cycloaddition. Notably, the construction of double isoxazoline moieties and two chiral centers including a spiro carbon center was achieved.

中文翻译：

通过双氧化氮与脲基酸酯的双1,3-偶极环加成直接获得螺索比恶唑啉†

已实现了腈氧化物和烯丙酸酯之间的双[3 + 2]-环加成反应。在DABCO与Et ₃ N结合存在的情况下，通过双1,3-偶极环加成反应，2-取代的buta-2,3-dienoates与肟氯化物反应，以55-90％的产率提供spirobiisoxazoazolines 。值得注意的是，实现了双异恶唑啉部分和两个包括螺碳中心的手性中心的构建。

更新日期：2018-01-04

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