Synthesis of Polysubstituted 2,3-Dihydrofurans via P(NMe2)3- Mediated [1＋4] Annulation of 1,2-Dicarbonyl Compounds with α,β-Unsaturated Ketones

doi:10.6023/cjoc202205021

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (11): 3805-3815.DOI: 10.6023/cjoc202205021 Previous Articles Next Articles

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P(NMe₂)₃介导1,2-二羰基化合物与α,β-不饱和酮的[1＋4]环化反应及多取代2,3-二氢呋喃的合成

薛飞雪^a, 曾建伟^a, 严泰山^a, 韩杰^a^,^*(), 贺峥杰^a^,^b^,^*()

^a南开大学化学学院元素有机化学国家重点实验室天津 300071
^b天津化学化工协同创新中心天津 300071

收稿日期:2022-05-16 修回日期:2022-07-05 发布日期:2022-07-13
通讯作者: 韩杰, 贺峥杰
基金资助:
国家自然科学基金(21472096); 国家自然科学基金(22171143)

Synthesis of Polysubstituted 2,3-Dihydrofurans via P(NMe₂)₃- Mediated [1＋4] Annulation of 1,2-Dicarbonyl Compounds with α,β-Unsaturated Ketones

Feixue Xue^a, Jianwei Zeng^a, Taishan Yan^a, Jie Han^a(), Zhengjie He^a^,^b()

^aState Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
^bCollaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071

Received:2022-05-16 Revised:2022-07-05 Published:2022-07-13
Contact: Jie Han, Zhengjie He
Supported by:
National Natural Science Foundation of China(21472096); National Natural Science Foundation of China(22171143)

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Abstract

A [1＋4] annulation of 1,2-dicarbonyl compounds with α,β-unsaturated ketones has been readily realized under the mediation of P(NMe₂)₃, producing polysubstituted 2,3-dihydrofurans bearing a quaternary carbon center in fair to good yields with a broad substrate scope. This reaction accordingly constitutes a new synthetic method for such compounds. In some cases, a [1＋2] annulation reaction competitively occurs, delivering polysubstituted cyclopropanes. With the aid of density functional theory (DFT) calculation, a plausible mechanism for the [1＋4] annulation and the chemoselectivity between [1＋2] and [1＋4] annulations has been discussed.

Key words: 1＋4] annulation, 1,2-dicarbonyl compounds, [1＋2] annulation, 2,3-dihydrofuran, Kukhtin-Remirez adduct

Cite this article

Feixue Xue, Jianwei Zeng, Taishan Yan, Jie Han, Zhengjie He. Synthesis of Polysubstituted 2,3-Dihydrofurans via P(NMe₂)₃- Mediated [1＋4] Annulation of 1,2-Dicarbonyl Compounds with α,β-Unsaturated Ketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3805-3815.

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P(NMe₂)₃介导1,2-二羰基化合物与α,β-不饱和酮的[1＋4]环化反应及多取代2,3-二氢呋喃的合成

Synthesis of Polysubstituted 2,3-Dihydrofurans via P(NMe₂)₃- Mediated [1＋4] Annulation of 1,2-Dicarbonyl Compounds with α,β-Unsaturated Ketones

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