镍催化的酰基咪唑与丙烯醛或 β 酯烯酮的不对称迈克尔加成反应

IF 3.8 3区 化学 Q2 CHEMISTRY, PHYSICAL ChemCatChem Pub Date : 2024-09-10 DOI:10.1002/cctc.202401324
Qian Shi, Jiani Sun, Jiangbo Wu, Xuehe Lu, Xiaoyu Wu
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引用次数: 0

摘要

在镍-双噁唑啉络合物的催化下,α-取代的酰基咪唑与丙烯醛发生了对映选择性迈克尔加成反应。事实证明,使用强路易斯酸 TMSOTf 作为活化迈克尔受体的添加剂对该工艺的成功至关重要。该工艺可容忍多种酰基咪唑,并以高产率和良好的对映选择性获得了一系列共轭加合物。除丙烯醛外,β-酯烯酮也适用于该工艺,在大多数情况下都能以高产率和良好的非对映选择性及对映选择性获得相应的共轭加合物。通过 2 毫摩尔规模的反应和衍生实验,证实了该反应体系的潜在实用性。
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Nickel‐Catalyzed Asymmetric Michael Addition of Acyl Imidazoles to Acrolein or β‐Ester Enones
An enantioselective Michael addition of α‐substituted acyl‐imidazoles to acrolein catalyzed by a nickel‐bisoxazoline complex has been developed. The use of strong Lewis acid TMSOTf as an additive to activate the Michael acceptors proved to be vital to the success of this process. This process tolerates a wide range of acyl‐imidazoles, and a series of conjugate adducts were obtained in high yields and good enantioselectivities. Besides acrolein, β‐ester ennones are also applicable in this process affording the corresponding conjugate adducts in high yields with good diastereoselectivities and enantioselectivites in most cases. The potential utility of the reaction system was confirmed through 2 mmol‐scale reaction and derivatization experiments.
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来源期刊
ChemCatChem
ChemCatChem 化学-物理化学
CiteScore
8.10
自引率
4.40%
发文量
511
审稿时长
1.3 months
期刊介绍: With an impact factor of 4.495 (2018), ChemCatChem is one of the premier journals in the field of catalysis. The journal provides primary research papers and critical secondary information on heterogeneous, homogeneous and bio- and nanocatalysis. The journal is well placed to strengthen cross-communication within between these communities. Its authors and readers come from academia, the chemical industry, and government laboratories across the world. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies, and is supported by the German Catalysis Society.
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