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Catalytic Direct Nucleophilic Substitution of Primary Morita–Baylis­–Hillman Adducts and Application to the Straightforward Synthesis of Dihydroisoindolones
Synthesis ( IF 2.2 ) Pub Date : 2017-11-14 , DOI: 10.1055/s-0036-1589131
Emmanuel Vrancken 1 , Marwa Ayadi 2 , Pierre Mpawenayo 1 , Farhat Rezgui 2 , Eric Leclerc 1 , Jean-Marc Campagne 1
Affiliation  

Abstract

An interesting γ-carbonyl effect permits the dual iron/boron-catalyzed direct nucleophilic substitution of functionalized primary allylic­ alcohols with a large variety of nucleophiles. The resulting substitution products are useful synthetic platforms for heterocycle synthesis, as illustrated in a ready access to tetrahydroisoindol-4-ones.

An interesting γ-carbonyl effect permits the dual iron/boron-catalyzed direct nucleophilic substitution of functionalized primary allylic­ alcohols with a large variety of nucleophiles. The resulting substitution products are useful synthetic platforms for heterocycle synthesis, as illustrated in a ready access to tetrahydroisoindol-4-ones.



中文翻译:

森田-贝利斯-希尔曼加合物的催化直接亲核取代及其在二氢异吲哚酮的简单合成中的应用

摘要

有趣的γ-羰基作用允许铁/硼催化的功能化伯烯丙基醇被多种亲核试剂双重铁/硼催化直接亲核取代。所得到的取代产物是用于杂环合成的有用的合成平台,如容易获得的四氢异吲哚-4-酮所示。

有趣的γ-羰基作用允许铁/硼催化的功能化伯烯丙基醇被多种亲核试剂双重铁/硼催化直接亲核取代。所得到的取代产物是用于杂环合成的有用的合成平台,如容易获得的四氢异吲哚-4-酮所示。

更新日期:2017-11-14
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