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

doi:10.6023/cjoc202203048

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2504-2514.DOI: 10.6023/cjoc202203048 Previous Articles Next Articles

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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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Abstract

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

Cite this article

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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Fig. & Tab. 4

References 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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