Catalytic asymmetric synthesis of trans-configured β-lactones: Cooperation of Lewis acid and ion pair catalysis

Kull T.; Cabrera J.; Peters R.

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Catalytic asymmetric synthesis of trans-configured β-lactones: Cooperation of Lewis acid and ion pair catalysis

机译：反式构型β-内酯的催化不对称合成：路易斯酸和离子对催化的协同作用

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The development of the first trans-selective catalytic asymmetric [2+2] cyclocondensation of acyl halides with aliphatic aldehydes furnishing 3,4-disubstituted β-lactones is described. This work made use of a new strategy within the context of asymmetric dual activation catalysis: it combines the concepts of Lewis acid and organic aprotic ion pair catalysis in a single catalyst system. The methodology could also be applied to aromatic aldehydes and offers broad applicability (29 examples). The utility was further demonstrated by nucleophilic ringopening reactions that provide highly enantiomerically enriched anti-aldol products.

机译：描述了酰基卤与具有3，4-二取代的β-内酯的脂族醛的第一反式选择性催化不对称[2 + 2]环缩合的发展。这项工作在不对称双活化催化的背景下利用了一种新的策略：它将路易斯酸和有机非质子离子对催化的概念结合在一个单一的催化剂体系中。该方法还可以应用于芳族醛，并具有广泛的适用性（29个示例）。通过亲核性开环反应进一步证明了该实用性，所述亲核性开环反应提供了高度对映体富集的抗醛醇缩合产物。

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《Chemistry: A European journal》 |2010年第30期|共8页
作者
Kull T.; Cabrera J.; Peters R.;
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正文语种 eng
中图分类应用化学;
关键词
Anti-aldol; Catalysis; Enolates; Ketenes; Pyridinium;

机译：抗羟醛;催化;烯醇盐;烯酮;吡啶鎓;

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1. Catalytic asymmetric synthesis of trans-configured β-lactones: Cooperation of Lewis acid and ion pair catalysis [J] . Kull T., Cabrera J., Peters R. Chemistry: A European journal . 2010,第30期

机译：反式构型β-内酯的催化不对称合成：路易斯酸和离子对催化的协同作用
2. Catalytic Asymmetric Synthesis of trans-Configured β-Lactones: Cooperation of Lewis Acid and Ion Pair Catalysis [J] . Thomas Kull Dr., Joseacute, Cabrera Dr., Chemistry - A European Journal . 2010,第30期

机译：构型β-内酯的催化不对称合成：路易斯酸和离子对催化的协同作用
3. Contact Ion Pair Directed Lewis Acid Catalysis: Asymmetric Synthesis of trans-Configured β-Lactones [J] . Thomas Kull, Rene Peters Angewandte Chemie . 2008,第29期

机译：接触离子对指导的路易斯酸催化：不对称合成反式β-内酯
4. CATALYTIC ASYMMETRIC SYNTHESIS OF CYCLOPROPANECARBOXYLIC ACIDS, AN APPLICATION TO INSECTICIDES SYNTHESIS [C] . T. Aratani, H. Yoshihara, T. Ageha International Congress of Pesticide Chemistry . 1986

机译：催化不对称合成环丙烷羧酸，杀虫剂合成施用
5. Highly Electrophilic Phosphorus(V) Cations as Robust Lewis Acids in Catalysis and Frustrated Lewis Pair Chemistry [D] . Bayne, Julia Margaret. 2019

机译：高热的磷（v）阳离子作为催化和沮丧的刘易斯对化学的鲁棒路易斯酸
6. Cooperative Al(Salen)-Pyridinium Catalysts for the Asymmetric Synthesis of trans-Configured β-Lactones by 2+2-Cyclocondensation of Acylbromides and Aldehydes: Investigation of Pyridinium Substituent Effects [O] . Patrick Meier, Florian Broghammer, Katja Latendorf, 2012

机译：配合使用的Al（Salen）-吡啶鎓催化剂通过酰基溴和醛的2 + 2-环缩合不对称合成反式配置的β-内酯：吡啶鎓取代基作用的研究
7. Asymmetric autocatalysis induced by meteoritic amino acids with hydrogen isotope chirality† †This article is part of a ChemComm ‘Catalysis in Organic Synthesis’ web-theme issue showcasing high quality research in organic chemistry. Please see our website (http://www.rsc.org/chemcomm/organicwebtheme2009) to access the other papers in this issue. ‡ ‡Electronic supplementary information (ESI) available: Procedures for the asymmetric autocatalysis in the presence of 1 and 2, the preparation of enantiomers of 1 and 2, and the determination of the enantiomeric purity of 1 and 2. See DOI: 10.1039/b908754k Click here for additional data file. [O] . Kawasaki, Tsuneomi, Shimizu, Masako, Nishiyama, Daisuke, 2009

机译：具有氢同位素手性的陨石氨基酸诱导的不对称自催化† †本文是ChemComm“有机合成催化”网络主题的一部分，该主题展示了有机化学的高质量研究。请访问我们的网站（http://www.rsc.org/chemcomm/organicwebtheme2009）以访问本期的其他论文。 ‡ 可用的电子补充信息（ESI）：在1和2存在下进行不对称自催化的过程，1和2对映体的制备以及1和2对映体纯度的测定。请参见DOI：10.1039 / b908754k 单击此处获取其他数据文件。

Catalytic asymmetric synthesis of trans-configured β-lactones: Cooperation of Lewis acid and ion pair catalysis

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