氮杂环卡宾(NHC)催化的联芳基二醛去对称化构建轴手性醛类化合物

doi:10.6023/cjoc202203048

有机化学 ›› 2022, Vol. 42 ›› Issue (8): 2504-2514.DOI: 10.6023/cjoc202203048 上一篇下一篇

研究论文

氮杂环卡宾(NHC)催化的联芳基二醛去对称化构建轴手性醛类化合物

赵薇^a, 刘京^a, 何向奎^a, 蒋豪^a, 陆良秋^a^,^b^,^*(), 肖文精^a^,^*()

a 华中师范大学化学学院武汉 430079
b 河南师范大学化学化工学院河南新乡 453007

收稿日期:2022-03-23 修回日期:2022-04-30 发布日期:2022-05-06
通讯作者: 陆良秋, 肖文精
基金资助:
国家自然科学基金(21822103); 国家自然科学基金(21820102003); 国家自然科学基金(91956201); 高等学校学科创新引智计划(111 Program); 高等学校学科创新引智计划(B17019); 湖北省自然科学基金(2017AHB047)

N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes

Wei Zhao^a, Jing Liu^a, Xiangkui He^a, Hao Jiang^a, Liangqiu Lu^a^,^b(), Wenjing Xiao^a()

a College of Chemistry, Central China Normal University, Wuhan 430079
b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2022-03-23 Revised:2022-04-30 Published:2022-05-06
Contact: Liangqiu Lu, Wenjing Xiao
Supported by:
National Natural Science Foundation of China(21822103); National Natural Science Foundation of China(21820102003); National Natural Science Foundation of China(91956201); Program of Introducing Talents of Discipline to Universities of China(111 Program); Program of Introducing Talents of Discipline to Universities of China(B17019); Natural Science Foundation of Hubei Province(2017AHB047)

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摘要/Abstract

在不对称催化合成领域, 轴手性醛类化合物因其独特的结构常作为有机催化剂或手性配体的前体, 发展其对映选择性与结构多样性的合成方法一直是化学家们的兴趣所在. 然而, 只有很少的催化方法被开发用于构建结构多样的轴手性醛. 利用去对称化策略, 通过卡宾催化的氧化酯化反应发展了一类轴手性醛类化合物的新合成方法. 该方法条件温和, 具有优异的产率和对映选择性, 且底物范围较广, 官能团兼容性较好. 这一策略为轴手性醛及其衍生物的合成提供了新的可能性.

关键词: 轴手性, 氮杂环卡宾催化, 去对称化

In the field of asymmetric catalytic synthesis, axially chiral aldehydes are often used as precursors of organic catalysts or chiral ligands because of their unique structures. The development of synthetic methods with enantioselectivity and structural diversity has always been the interest of chemists. However, only few catalytic methods have been developed for the construction of structurally diverse axially chiral aldehydes. Herein, a N-heterocyclic carbene (NHC)-catalyzed oxidative esterification reaction to synthesize axially chiral aldehydes through desymmetrization strategy was developed. This method features mild conditions (room temperature), excellent yields and enantioselectivity, broad substrate scope and good function group tolerance (26 examples, 54%~97% yields, up to 99% ee). All the axially chiral aldehyde products have been fully characterized and the absolute configuration was established by comparing the results from known literature. This strategy provides new possibilities for the synthesis of axially chiral aldehydes and their derivatives.

Key words: axially chiral, N-heterocyclic carbene, desymmetrization

引用此文

赵薇, 刘京, 何向奎, 蒋豪, 陆良秋, 肖文精. 氮杂环卡宾(NHC)催化的联芳基二醛去对称化构建轴手性醛类化合物[J]. 有机化学, 2022, 42(8): 2504-2514.

Wei Zhao, Jing Liu, Xiangkui He, Hao Jiang, Liangqiu Lu, Wenjing Xiao. N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2504-2514.

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参考文献 15

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Entry	Deviation from standard conditions	Yield^b/% of 3aa	ee^c/% of 3aa
1	None	97	>99
2	NHC-2 instead of NHC-1	27	65
3	NHC-3 instead of NHC-1	56	76
4	NHC-4 instead of NHC-1	5	2
5	NHC-5 instead of NHC-1	33	36
6	MnO₂instead of DQ	59	80
7	O₂instead of DQ	64	90
8	THF instead of toluene	86	80
9	CH₃CN instead of toluene	79	99
11	DABCO instead of K₂CO₃	NR	ND
12	Cs₂CO₃ instead of K₂CO₃	85	>99
13	Na₂HPO₄ instead of K₂CO₃	NR	ND
14	Na₂CO₃ instead of K₂CO₃	7	29

Entry	Deviation from standard conditions	Yield^b/% of 3aa	ee^c/% of 3aa
1	None	97	>99
2	NHC-2 instead of NHC-1	27	65
3	NHC-3 instead of NHC-1	56	76
4	NHC-4 instead of NHC-1	5	2
5	NHC-5 instead of NHC-1	33	36
6	MnO₂instead of DQ	59	80
7	O₂instead of DQ	64	90
8	THF instead of toluene	86	80
9	CH₃CN instead of toluene	79	99
11	DABCO instead of K₂CO₃	NR	ND
12	Cs₂CO₃ instead of K₂CO₃	85	>99
13	Na₂HPO₄ instead of K₂CO₃	NR	ND
14	Na₂CO₃ instead of K₂CO₃	7	29

氮杂环卡宾(NHC)催化的联芳基二醛去对称化构建轴手性醛类化合物

N-Heterocyclic Carbene (NHC)-Catalyzed Desymmetrization of Biaryldialdehydes to Construct Axially Chiral Aldehydes

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