了解噁唑硼烷离子催化的、以环丁烯酮为亲二烯的 Diels-Alder 反应的反应性和选择性。

IF 3 4区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY ChemPlusChem Pub Date : 2024-11-25 DOI:10.1002/cplu.202400684
Susana Portela, Israel Fernández
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引用次数: 0

摘要

通过密度泛函理论计算,详细分析了控制以环丁烯酮为亲二烯催化的 Diels-Alder 反应的反应性和选择性(立体选择性和对映体选择性)的未知因素。为此,我们选择了科里的手性噁唑硼烷离子(COBI)催化的环戊二烯和呋喃作为二烯和 3-(甲氧基羰基)环丁烯酮的反应,并将其与类似的非催化转化进行了比较。采用反应活化应变模型和能量分解分析相结合的方法,定量地了解了催化剂在该转化过程中诱导的加速度和选择性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Understanding the Reactivity and Selectivity of Oxazaborolidium Ion-Catalyzed Diels-Alder Reactions Involving Cyclobutenones as Dienophiles

The poorly understood factors controlling the reactivity and selectivity (both stereo- and enantioselectivity) of catalyzed Diels-Alder reactions involving cyclobutenones as dienophiles have been analyzed in detail by means of Density Functional Theory calculations. To this end, the reactions with cyclopentadiene and furan as dienes and 3-(methoxycarbonyl)cyclobutenone catalyzed by Corey's chiral oxazaborolidium ion (COBI) have been selected and compared to their analogous uncatalyzed transformations. The combined Activation Strain Model of reactivity and Energy Decomposition Analysis methods have been used to quantitatively understand the acceleration and selectivity induced by the catalyst in this reaction.

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来源期刊
ChemPlusChem
ChemPlusChem CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
5.90
自引率
0.00%
发文量
200
审稿时长
1 months
期刊介绍: ChemPlusChem is a peer-reviewed, general chemistry journal that brings readers the very best in multidisciplinary research centering on chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. Fully comprehensive in its scope, ChemPlusChem publishes articles covering new results from at least two different aspects (subfields) of chemistry or one of chemistry and one of another scientific discipline (one chemistry topic plus another one, hence the title ChemPlusChem). All suitable submissions undergo balanced peer review by experts in the field to ensure the highest quality, originality, relevance, significance, and validity.
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