Stereoselective Formation of Triphenylene Ketals

Boshta NM; Bomkamp M; Schnakenburg G; Waldvogel SR

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Stereoselective Formation of Triphenylene Ketals

机译：三亚苯基缩酮的立体选择性形成

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摘要

The oxidative trimerization of catechol ketals by MoCl5 or MoCl5/TiCl4 mixtures leads preferentially to the all-syn stereoisomer of the corresponding triphenylene ketal. The concomitant metal salts of the oxidative coupling most probably form a multinuclear template that directs the diastereoselectivity in a subsequent isomerization step under electrophilic conditions. Several functionalities can serve as coordination sites for the multinuclear metal chloro clusters. Suitable functional groups have to be stable towards the strong electrophilic and oxidizing conditions. Therefore, esters, nitriles, nitro derivatives, triazoles, and pyridines are successfully employed. Based on the flexibility and size of the substrate, different reagent mixtures lead to the stereoselective formation of the all-syn derivatives.

机译：MoCl5或MoCl5 / TiCl4混合物对邻苯二酚缩酮的氧化三聚作用优先导致相应的三亚苯基缩酮的全顺式立体异构体。氧化偶合的伴随金属盐最有可能形成多核模板，该模板指导在亲电条件下随后的异构化步骤中的非对映选择性。多种功能可以用作多核金属氯簇的配合位点。合适的官能团必须对强亲电和氧化条件稳定。因此，成功地使用了酯，腈，硝基衍生物，三唑和吡啶。根据底物的柔韧性和大小，不同的试剂混合物会导致全合成衍生物的立体选择性形成。

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《Chemistry: A European journal》 |2010年第11期|共8页
作者
Boshta NM; Bomkamp M; Schnakenburg G; Waldvogel SR;
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正文语种 eng
中图分类应用化学;
关键词
CC coupling; diastereoselectivity; molybdenum; oxidation; triphenylene ketal;

机译：CC耦合;非对映选择性;钼;氧化;三亚苯基缩酮;

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1. Stereoselective Formation of Triphenylene Ketals [J] . Boshta NM, Bomkamp M, Schnakenburg G, Chemistry: A European journal . 2010,第11期

机译：三亚苯基缩酮的立体选择性形成
2. Total synthesis of(-)-centrolobine:beta-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction [J] . Michael P.Jennings, Ryan T.Clemens Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2005,第12期

机译：通过串联格利雅加和立体选择性半缩酮还原法合成（-）-中心叶素：β-C-糖苷的总合成
3. Total synthesis of(-)-centrolobine:beta-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction [J] . Michael P.Jennings, Ryan T.Clemens Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2005,第12期

机译：通过串联格利雅加和立体选择性半缩酮还原法合成（-）-中心叶素：β-C-糖苷的总合成
4. An infrared technique for the alignment control of highly viscous mesophases: The formation of homeotropic and planar domains for hexagonal columnar mesophase of Triphenylene mesogens [C] . Y. Shimizu, H. Monobe, H.Hori, Liquid Crystals IX . 2005

机译：红外技术，用于高粘度中间相的取向控制：三亚苯基介晶的六方柱状中间相的垂直和平面畴的形成
5. Synthesis of side chain-modified iodothyronines. Synthesis and structure-activity relationships (SARS) of galanthamine derivatives. Total synthesis of (+)-valyldetoxinine. Synthesis and mechanism of cyclic acetal and ketal formation in pentono-1,4-lactones. [D] . Han, So-Yeop. 1992

机译：侧链修饰的碘甲状腺素的合成。加兰他敏衍生物的合成及其构效关系（SARS）。（+）-Valyldetoxinine的全合成。戊通-1,4-内酯中环状缩醛和缩酮的合成及其机理。
6. A Simple and Versatile Method for the Formation ofAcetals/Ketals Using Trace Conventional Acids [O] . Jian-Lian Dong, Li-Si-Han Yu, Jian-Wu Xie, 2018

机译：一种简单而通用的形成方法使用痕量常规酸的缩醛/缩酮
7. Dendritic compound of triphenylene-2,6,10-trione ketal-tri-{2,2-di-[(N-methyl-N-(4-pyridinyl) amino) methyl]-1,3-propanediol}: an easily recyclable catalyst for Morita-Baylis-Hillman reactions [O] . Yan-Ru Zang, Rong-Bao Wei, Hong-Lin Li, 2009

机译：三亚苯基-2,6,10-酮缩酮-三{2,2-二-[（N-甲基-N-（4-吡啶基）氨基）甲基] -1,3-丙二醇}的树枝状化合物Morita-Baylis-Hillman反应的可回收催化剂

Stereoselective Formation of Triphenylene Ketals

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