Stereocontrolled desymmetrization of 2,5-cyclohexadienones via organocatalytic domino sulfa-1,6-/1,4-addition or sulfa-1,6- /1,4-/sulfa-1,4-addition reactions

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-14 DOI:10.1039/d4qo02097a

Vanisha Sodhi, Deepak Sharma, Manisha Sharma, Pankaj Chauhan

引用次数: 0

Abstract

We have developed a desymmetrization of 2,5-cyclohexadienones tethered 3-cyano-4-styrylcoumarins via the amino-squaramide catalyzed initial regio-/enantio-selective sulfa-1,6-addition to the 3-cyano-4-styrylcoumarin moiety of the substrate, followed by an intramolecular vinylogous 1,4-addition to the dienone portion. An additional sulfa-Michael addition was observed when the thiols were taken in excess to create an additional stereogenic center. With our divergent approach, the two unique classes of hydrophenanthrene skeletons have been synthesized as single diastereoisomers in good to excellent yields and enantioselectivities (up to >99.5:0.5 er).

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通过有机催化多米诺磺胺-1,6-/1,4-加成或磺胺-1,6-/1,4-/磺胺-1,4-加成反应实现 2,5-Cyclohexadienones 的立体可控非对称化

我们开发了一种 2,5-Cyclohexadienones tetherted 3-Cyano-4-styrylcoumarins 的去对称化方法，该方法通过氨基夸父酰胺催化，使底物的 3-Cyano-4-styrylcoumarin 分子发生最初的区域/对映选择性磺基-1,6-加成，然后二烯酮部分发生分子内乙烯基-1,4-加成。当硫醇过量产生额外的立体中心时，还能观察到磺胺-迈克尔加成反应。通过我们的发散性方法，我们合成出了两类独特的氢菲骨架非对映异构体，产量和对映选择性都非常好（高达 99.5:0.5er）。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.