Construction of cyclopenta[b]pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes,Organic Chemistry Frontiers

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Construction of cyclopenta[b]pyran-2-ones via chemoselective (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2020/02/19 , DOI: 10.1039/d0qo00049c
Xuefeng Liang _{1,

2,

3,

4} , Weijian Ye _{1,

2,

3,

4} , Waygen Thor _{5,

6,

7,

8} , Lantian Sun _{5,

6,

7,

8} , Bo Wang _{5,

6,

7,

8} , Shuzhong He _{4,

9,

10,

11} , Yuen-Kit Cheng _{5,

6,

7,

8} , Chi-Sing Lee _{1,

2,

3,

4,

5}

Affiliation

A method for synthesising cyclopenta[b]pyran-2-ones through direct (3 + 2) cycloaddition between 2-pyrones and vinyl cyclopropanes is described. In the presence of Pd₂(dba)₃/dppe in toluene, a series of 2-pyrones undergo chemoselective (3 + 2) cycloaddition with vinyl cyclopropanes and afford cyclopenta[b]pyran-2-ones in high yields (78–96%). The trans/cis ratio of the cycloadducts has been optimised up to 10 : 1. The proposed mechanism of this cycloaddition has been rationalised by computational studies.

中文翻译：

通过2-吡喃酮和乙烯基环丙烷之间的化学选择性（3 + 2）环加成反应构建环戊[b]吡喃-2-酮

描述了通过在2-吡喃酮和乙烯基环丙烷之间的直接（3 + 2）环加成来合成环戊[ b ]吡喃-2-酮的方法。在甲苯中存在Pd ₂（dba）₃ / dppe的情况下，一系列2-吡喃酮与乙烯基环丙烷进行化学选择（3 + 2）环加成反应，并以高收率获得环戊[ b ] pyran-2-ones（78-96）％）。环加合物的反式/顺式比例已优化至10：1。该环加成反应的拟议机理已通过计算研究合理化。

更新日期：2020-03-19

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