Chromium-catalyzed pinacol-type cross-coupling: Studies on stereo selectivity

Groth U; Jung M; Vogel T

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Chromium-catalyzed pinacol-type cross-coupling: Studies on stereo selectivity

机译：铬催化的频哪醇型交叉偶联：立体选择性研究

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A chromium-catalyzed pinacol-type cross-coupling reaction between α,β-unsaturated carbonyl compounds and aldehydes is reported. Even sterically demanding substrates could be coupled to afford the corresponding pinacols in good yields. Systematic studies concerning the origin of the diastereoselectivities led to the proposal of a mechanism for this synthetically useful reaction. Acroleins with ubranched alkyl side chains were coupled to give the corresponding syn pinacols, while on the other hand, acroleins with less bulky substituents furnished the anti derivatives. The effects of both the substrates and the reagents on the diastereo- and enantioselectivities were investigated. An unexpected catalytic formation of cyclopropanols was found.

机译：报道了α，β-不饱和羰基化合物与醛之间的铬催化的频哪醇型交叉偶联反应。甚至对空间要求严格的基板也可以进行耦合，从而以良好的产量提供相应的频哪醇。有关非对映选择性起源的系统研究导致提出了这种合成上有用的反应的机制。将具有未支化烷基侧链的丙烯醛偶联以得到相应的顺式频哪醇，而另一方面，具有较小体积取代基的丙烯醛提供了反衍生物。研究了底物和试剂对非对映选择性和对映选择性的影响。发现环丙醇意外地催化形成。

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《Chemistry: A European journal》 |2005年第10期|共9页
作者
Groth U; Jung M; Vogel T;
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正文语种 eng
中图分类化学;
关键词
chromium; cross-coupling; diastereoselectivity; homogeneous catalysis; pinacols; LEAF GROWTH-ACTIVITY; ALPHA; BETA-UNSATURATED KETONES; CARBONYL-COMPOUNDS; ORGANIC-SYNTHESIS; ASYMMETRIC DIHYDROXYLATION; FUNGAL METABOLITE; ALDEHYDES; CONDENSATION; COMPLEXES; SYSTEM;

机译：铬;交叉偶联;非对映选择性;均相催化;松果;叶生长活性;α;贝塔不饱和酮;羰基化合物;有机合成;不对称二羟基氧化;真菌;缩醛;缩醛;

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1. Chromium-catalyzed pinacol-type cross-coupling: Studies on stereo selectivity [J] . Groth U, Jung M, Vogel T Chemistry: A European journal . 2005,第10期

机译：铬催化的频哪醇型交叉偶联：立体选择性研究
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4. Mechanistic Studies for Chromium-catalyzed Cyclopropanation ofAlkenes in the Presence of Organosilicon Compounds as aReductant [C] . Hideaki Ikeda, Kohei Nishi, Hayato Tsurugi 日本化学会春季年会 . 2020

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Chromium-catalyzed pinacol-type cross-coupling: Studies on stereo selectivity

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