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Experimental and theoretical studies on the hydrogen-bond-promoted enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with benzaldehyde.关于丹尼谢夫斯基双烯与苯甲醛的氢键促进对映选择性杂Diels-Alder反应的实验与理论研究
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Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding.轴手性联芳基二醇通过氢键催化高度对映选择性的杂Diels-Alder反应。
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A computational study of the Diels-Alder reaction of ethyl-S-lactyl acrylate and cyclopentadiene. Origins of stereoselectivity.乙基-S-乳酸丙烯酸酯与环戊二烯的狄尔斯-阿尔德反应的计算研究。立体选择性的起源。
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Enhancing reactivity of carbonyl compounds via hydrogen-bond formation. A DFT study of the hetero-Diels-Alder reaction between butadiene derivative and acetone in chloroform.通过氢键形成增强羰基化合物的反应活性。氯仿中丁二烯衍生物与丙酮之间杂环狄尔斯-阿尔德反应的密度泛函理论研究。
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Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones.
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氢键催化通过在高度极性的狄尔斯-阿尔德反应中实现电荷稳定来发挥作用。

Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.

作者信息

Gordillo Ruth, Dudding Travis, Anderson Christopher D, Houk K N

机构信息

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

出版信息

Org Lett. 2007 Feb 1;9(3):501-3. doi: 10.1021/ol0629925.

DOI:10.1021/ol0629925
PMID:17249797
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2531143/
Abstract

[reaction: see text] The alcohol-catalyzed Diels-Alder reactions of acrolein and benzaldehyde with Rawal's diene were evaluated with density functional theory (B3LYP/6-31G(d)). Several potential modes of catalysis with two methanol molecules were used to model catalysis by TADDOLs. In agreement with crystallographic data, cooperative catalysis with TADDOLs is predicted to be favorable.

摘要

[反应：见正文] 采用密度泛函理论（B3LYP/6-31G(d)）评估了丙烯醛和苯甲醛与拉瓦尔二烯的醇催化狄尔斯-阿尔德反应。使用两个甲醇分子的几种潜在催化模式来模拟TADDOLs的催化作用。与晶体学数据一致，预计TADDOLs的协同催化是有利的。