Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium salts to synthesize thiazole and 1,4-thiazine derivatives†,Organic Chemistry Frontiers

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Enantioselective [3 + 2] cycloaddition and rearrangement of thiazolium salts to synthesize thiazole and 1,4-thiazine derivatives†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-05-28 00:00:00 , DOI: 10.1039/c8qo00370j
Xiying Zhang _{1,

2,

3,

4,

5} , Xiaohua Liu _{1,

2,

3,

4,

5} , Jianlin Zhang _{1,

2,

3,

4,

5} , Dong Zhang _{1,

2,

3,

4,

5} , Lili Lin _{1,

2,

3,

4,

5} , Xiaoming Feng _{1,

2,

3,

4,

5}

Affiliation

Highly efficient asymmetric [3 + 2] cycloaddition reactions of thiazolium salts with a variety of electron-deficient 2-π components were achieved by chiral N,N′-dioxide/metal complex catalysts, providing a convenient route to access enantioenriched hydropyrrolo-thiazoles. The oxathiazine and sulfinate could be readily obtained by the oxidation of the hydropyrrolo-thiazole. Moreover, through ingenious collaboration of chiral catalysts with basic additives, the first cascade cycloaddition/rearrangement reaction with β,γ-unsaturated α-ketoesters was realized, and various pyrrolo-[1,4]thiazine derivatives were afforded in excellent results.

中文翻译：

噻唑盐的对映选择性[3 + 2]环加成和重排，以合成噻唑和1,4-噻嗪衍生物†

通过手性N，N'-二氧化物/金属络合物催化剂，可实现噻唑鎓盐与多种电子不足的2-π组分的高效不对称[3 + 2]环加成反应，为获得对映体富集的氢吡咯并噻唑提供了便利的途径。氧杂吡咯并噻唑的氧化可容易地获得草并噻嗪和亚磺酸盐。此外，通过手性催化剂与碱性添加剂的巧妙配合，实现了与β，γ-不饱和α-酮酸酯的第一级联环加成/重排反应，并得到了各种吡咯-[1,4]噻嗪衍生物。

更新日期：2018-05-28

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