β,γ-不饱和吡唑酰胺与 MBH 碳酸盐之间的有机催化对映体选择性乙烯基烯丙基烷基化反应

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-10-14 DOI:10.1002/ejoc.202400799

Yun-Peng He, Jun-Hao Fu, Feng Sha, Xin-Yan Wu

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引用次数: 0

摘要

直接不对称乙烯基烯丙基烷基化是构建手性 1,5 二烯化合物的有效方法。在这项研究中，无环不饱和酰胺被用作对映选择性乙烯基烯丙基烷基化反应的亲核剂。在使用 10 mol% 手性叔胺 C11 的情况下，β,γ-不饱和吡唑酰胺与 Morita-Baylis-Hillman 碳酸酯之间实现了对映选择性乙烯基烯丙基烷基化反应，得到了具有光学活性的多功能手性 1,5-二烯化合物，收率为中等到极好（74-99%），对映选择性为良好到极好（67-94% ee）。

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Organocatalytic Enantioselective Vinylogous Allylic Alkylation between β,γ-Unsaturated Pyrazoleamides and MBH Carbonates

The direct asymmetric vinylogous allylic alkylation is an efficient method to construct chiral 1,5-diene compounds. In this work, acyclic unsaturated amides are used as a nucleophile for enantioselective vinylogous allylic alkylation. With 10 mol% of chiral tertiary amine C11, the enantioselective vinylogous allylic alkylation between β,γ-unsaturated pyrazoleamides and Morita-Baylis-Hillman carbonates is achieved, affording optically active multifunctional chiral 1,5-dienes in moderate to excellent yields (74-99%) with good-to-excellent enantioselectivities (67-94% ee).

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.