Chiral phosphoric acid catalyzed peroxidation of imines.
Chiral phosphoric acid catalyzed peroxidation of imines.
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DOI：
10.1002/anie.201002972
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发表时间：
2010-09-03
影响因子：
16.6
通讯作者：
Antilla, Jon C.
中科院分区：
文献类型：
--
作者：
Zheng, Wenhua;Wojtas, Lukasz;Antilla, Jon C.
含过氧化物的化合物是一类重要的生物靶标，其中许多具有抗肿瘤、抗菌和抗疟疾活性。[1]例如，含有过氧化物的天然产物青蒿素（青蒿素）已被证明是一种高效的抗疟疾药物。[2]这种天然产物中的手性过氧化物部分被证明是高抗疟效力所必需的。[2]因此，手性过氧化物的立体选择性制备方法和策略的发展对化学和药物合成的从业者变得相当重要。然而，手性过氧化物的催化合成仍然是合成化学家的一个具有挑战性的目标。[3-5]2008年，Deng [6]和List [7]的研究组分别报道了手性碱催化的α，β-不饱和酮的对映选择性过氧化反应。例如，verruculogen（图1）含有α-氨基过氧化物，并已发现改变GABA受体结合和抑制哺乳动物细胞周期。[1a]此外，二氧杂环丁烷酮是一种高能天然产物，含有日本萤火虫中发现的手性α-氨基过氧化物。[8]据我们所知，没有催化不对称方法可以直接获得手性α-氨基过氧化物。[9]第一章
Peroxide-containing compounds are a class of biologically important targets, many of which possess antitumor, anti-bacterial, and antimalarial activities.[1] For example, the peroxidecontaining natural product artemisinin (qinghaosu) has been shown to be a highly effective antimalarial drug.[2] The chiral peroxide moiety in this natural product was proven to be essential for the high antimalarial potency.[2] For this reason, the development of stereoselective methods and strategies for the preparation of chiral peroxides has become considerably important to the practitioners of chemical and pharmaceutical synthesis. However, catalytic syntheses of chiral peroxides is still a challenging goal to synthetic chemists.[3–5] Despite these challenges, the groups of Deng [6] and List [7] independently reported the use of a chiral base-catalyzed enantioselective peroxidation of α, β-unsaturated ketones in 2008.Chiral α-amino peroxide moieties, though somewhat rare, can be found in natural products. For example, verruculogen (Figure 1) contains an α-amino peroxide, and has been found to alter GABA receptor binding and inhibit the mammalian cell cycle.[1a] In addition, dioxetanone is a high-energy natural product containing a chiral α-amino peroxide found in the Japanese firefly.[8] To the best of our knowledge, there is no catalytic asymmetric method that can give direct access to chiral α-amino peroxides.[9]
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影响因子：
15
作者：
Chung, Lung Wa;Hayashi, Shigehiko;Morokuma, Keiji
通讯作者：
Morokuma, Keiji
通过布朗斯台德酸催化的对映选择性氧化-迈克尔反应进行环己二烯酮的去对称化
影响因子：
15
作者：
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影响因子：
3.6
作者：
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通讯作者：
Woller, KR
影响因子：
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作者：
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通讯作者：
You, Shu-Li
影响因子：
16.6
作者：
Akiyama, Takahiko;Katoh, Takuya;Mori, Keiji
通讯作者：
Mori, Keiji