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首页> 外文期刊>Chemistry: A European journal >Organocatalytic Addition on 1,2-BisACHTUNGTRENUNG(sulfone)vinylenes Leading to an Unprecedented Rearrangement
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Organocatalytic Addition on 1,2-BisACHTUNGTRENUNG(sulfone)vinylenes Leading to an Unprecedented Rearrangement

机译：1,2-BisACHTUNGTRENUNG（砜）亚乙烯基的有机催化加成导致空前的重排

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The last decade has seen a rapid and fruitful growth of organocatalysis. By allowing new modes of molecular activation, in often mild and non-anhydrous conditions, these organocatalysed reactions appear as a method of choice for its future use in industry.[1] Among the numerous catalytic activation modes, aminocatalysis, one of the most extensively studied has lead to numerous methodologies notably describing the asymmetric a-functionalization of carbonyl compounds. A large part of the research on this subject has been carried out with the aim to discover new nucleophile/ electrophile combinations notably by conjugated addition that leads to the discovery of valuable synthons, and in few steps to natural products precursors.[2] Despite this impressive progress, the enantioselective direct a-alkylation of aldehydes and ketones remains a challenging task. Few reports have appeared recently on this subject and they still remain limited to specific substrates.[3] Another alternative method toward this a-alkylation has been developed in our group; this method makes use of the Michael addition on bis-activated substrates, such as 1,1-bisACHTUNGTRENUNG(sulfone)vinylenes and 1,1-bis(phosphonate)vinylenes.[4] Indeed, sulfones are highly valuable functionalities due to the great versatility of the sulfonyl group, which can undergo numerous transformations and can easily be cleaved at various synthetic stages.[5] In view of expanding the range of these highly tunable products, we wondered about using more versatile Michael adducts. Since we had previously shown that a single sulfone was not sufficient to undergo the enamine attack, we wondered if a 1,2-bisACHTUNGTRENUNG(sulfone)vinylene (IUPAC name: {[(E/Z)-2(phenylsulfonyl)ethenyl]sulfonyl}benzene) could accelerate the reaction leading to two different tunable functionalities.
机译：在过去的十年中，有机催化取得了快速而富有成果的增长。通过在温和的和无水的条件下允许新的分子活化方式，这些有机催化的反应成为其未来工业应用的一种选择方法。[1]在众多的催化活化方式中，氨基催化是研究最广泛的方法之一，已导致产生了许多方法，特别是描述了羰基化合物的不对称α-官能化。已经进行了有关该主题的大部分研究，目的是发现新的亲核试剂/亲电试剂组合，特别是通过共轭加成，从而发现有价值的合成子，并在很少的步骤中获得天然产物前体。[2]尽管取得了令人瞩目的进展，但醛和酮的对映选择性直接α-烷基化仍然是一项艰巨的任务。最近关于该主题的报道很少，但仍然仅限于特定的研究对象。[3]我们小组已经开发出另一种替代方法来处理这种α-烷基化反应。该方法利用了在双活化底物上的迈克尔加成反应，例如1,1-双ACHTUNGTRENUNG（砜）亚乙烯基和1,1-双（膦酸酯）亚乙烯基。[4]确实，由于磺酰基的多功能性强，砜是非常有价值的功能，它可以进行许多转化，并且可以在各种合成阶段轻松裂解。[5]为了扩大这些高度可调产品的范围，我们想知道是否使用功能更广泛的迈克尔加合物。由于我们以前已经证明单个砜不足以进行烯胺攻击，因此我们想知道1,2-bisACHTUNGTRENUNG（砜）亚乙烯基（IUPAC名称：{[（（E / Z）-2（phenylsulfonyl）ethenyl] ulfonyl }苯）可以加速反应，从而导致两个不同的可调功能。

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