Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives†,Organic Chemistry Frontiers

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Organocatalytic asymmetric [3 + 2] annulation of 1,4-dithiane-2,5-diol with azlactones: access to chiral dihydrothiophen-2(3H)-one derivatives†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-05-09 00:00:00 , DOI: 10.1039/c8qo00305j
Ji-cong Yu _{1,

2,

3,

4} , Le-mao Yu _{1,

2,

3,

4} , Xiao-yun Zhao _{1,

2,

3,

4} , Lu Gan _{1,

2,

3,

4} , Wei-wei Zhu _{1,

2,

3,

4} , Ze-chen Wang _{1,

3,

4,

5} , Rui Wang _{4,

6,

7,

8,

9} , Xianxing Jiang _{1,

2,

3,

4}

Affiliation

Herein, the first organocatalyst-mediated enantioselective [3 + 2] annulations of 1,4-dithiane-2,5-diol with various azlactones utilizing C4 and C5 reactivity using squaramide as the catalyst in a ring-opening manner have been reported. This protocol provides convenient access to enantioenriched substituted dihydrothiophen-2(3H)-one derivatives. Excellent isolated yields and moderate to good enantioselectivities have been achieved.

中文翻译：

1,4-二硫代-2,5-二醇与a内酯的有机催化不对称[3 + 2]环化反应：获得手性二氢噻吩-2（3 H）-一衍生物†

在本文中，已经报道了第一批有机催化剂介导的1，4-二噻吩-2，5-二醇与各种氮杂内酯的对映体选择[3 + 2]环化，该反应使用方酰胺以开环方式利用C4和C5反应性进行C4和C5反应性。该协议为对映体富集的取代的二氢噻吩-2（3 H）-one衍生物提供了方便的访问途径。已获得优异的分离产率和中等至良好的对映选择性。

更新日期：2018-05-09

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