cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)

doi:10.6023/cjoc202311002

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1535-1548.DOI: 10.6023/cjoc202311002 Previous Articles Next Articles

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银催化环状Morita-Baylis-Hillman醇及其类似物与芳基乙烯的顺式[5＋2]环加成反应研究

崔永伟, 梁春苗, 祝海涛^*(), 申成平, 任飞扬, 孙梦涵, 赵媛, 王文静, 王冬梅^*(), 周妮妮^*()

宝鸡文理学院化学化工学院陕西省植物化学重点实验室陕西宝鸡 721013

收稿日期:2023-11-02 修回日期:2024-01-17 发布日期:2024-02-07
基金资助:
陕西省自然科学基金(2021JQ-802); 陕西省教育厅科研计划(21JK0476); 陕西省创新能力推进计划(2022TD-63); 秦岭药用植物及有机功能分子研究与开发利用创新团队资助项目

cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)

Yongwei Cui, Chunmiao Liang, Haitao Zhu(), Chengping Shen, Feiyang Ren, Menghan Sun, Yuan Zhao, Wenjing Wang, Dongmei Wang(), Nini Zhou()

College of Chemistry and Chemical Engineering, Shannxi Key Laboratory of Phytochemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013

Received:2023-11-02 Revised:2024-01-17 Published:2024-02-07
Contact: *E-mail: zhuhaitaobwl@163.com; zhouni13_2008@163.com; wangdongmay@163.com
Supported by:
Natural Science Foundation of Shaanxi Province(2021JQ-802); Scientific Research Program Funded by Shaanxi Provincial Education Department(21JK0476); Innovation Capability Support Program of Shaanxi Province(2022TD-63); Innovation R&D Team of BUAS on Qinling Medicinal Plants and Functional Organic Molecules

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Abstract

An AgSbF₆-catalyzed diastereoselective [5＋2]-cycloaddition reaction was developed as an efficient entry into indanone-fused benzo[7]annulene frameworks from cyclic Morita-Baylis-Hillman alcohols and its analogues with aryl- ethylenes. Density functional theory (DFT) calculation data analysis shows that 1,3-cis-selectivity might be mainly controlled by kinetics. The resulting dihydrodibenzo[a,f]azulen-12-one 3a can be further functionalized by using the regioselective hydrogenation and cyclopropanation.

Key words: Morita-Baylis-Hillman alcohol, arylethylenes, silver catalysis, [5＋2]-cycloaddition

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Yongwei Cui, Chunmiao Liang, Haitao Zhu, Chengping Shen, Feiyang Ren, Menghan Sun, Yuan Zhao, Wenjing Wang, Dongmei Wang, Nini Zhou. cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1535-1548.

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Entry	Catalyst (dosage/mol%)	Solvent	Yield^b/%
1	p-TsOH•H₂O (15)	CH₂Cl₂	53
2	HNTf₂ (15)	CH₂Cl₂	83
3	HSbF₆ (15)	CH₂Cl₂	79
4	AgNTf₂ (15)	CH₂Cl₂	21
5	AgBF₆(15)	CH₂Cl₂	9
6	Sc(OTf)₃ (15)	CH₂Cl₂	50
7	FeCl₃ (15)	CH₂Cl₂	84
8	AgOTf (15)	CH₂Cl₂	Trace
9	Cu(OTf)₂ (15)	CH₂Cl₂	ND
10	PdCl₂ (15)	CH₂Cl₂	ND
11	AgSbF₆ (15)	CH₂Cl₂	89
12	AgSbF₆ (15)	ClCH₂CH₂Cl	81
13	AgSbF₆ (15)	CHCl₃	46
14	AgSbF₆ (15)	PhCH₃	32
15	AgSbF₆ (15)	CH₃CN	ND
16	AgSbF₆ (15)	THF	ND
17	AgSbF₆ (10)	CH₂Cl₂	85
18	AgSbF₆ (20)	CH₂Cl₂	88
19^c	AgSbF₆ (15)	CH₂Cl₂	57
20^d	AgSbF₆ (15)	CH₂Cl₂	ND
21^e	AgSbF₆ (15)	CH₂Cl₂	88
22^f	AgSbF₆ (15)	CH₂Cl₂	74
23^g	AgSbF₆ (15)	CH₂Cl₂	87
24^h	AgSbF₆ (15)	CH₂Cl₂	85
25ⁱ	AgSbF₆ (15)	CH₂Cl₂	79

Entry	Catalyst (dosage/mol%)	Solvent	Yield^b/%
1	p-TsOH•H₂O (15)	CH₂Cl₂	53
2	HNTf₂ (15)	CH₂Cl₂	83
3	HSbF₆ (15)	CH₂Cl₂	79
4	AgNTf₂ (15)	CH₂Cl₂	21
5	AgBF₆(15)	CH₂Cl₂	9
6	Sc(OTf)₃ (15)	CH₂Cl₂	50
7	FeCl₃ (15)	CH₂Cl₂	84
8	AgOTf (15)	CH₂Cl₂	Trace
9	Cu(OTf)₂ (15)	CH₂Cl₂	ND
10	PdCl₂ (15)	CH₂Cl₂	ND
11	AgSbF₆ (15)	CH₂Cl₂	89
12	AgSbF₆ (15)	ClCH₂CH₂Cl	81
13	AgSbF₆ (15)	CHCl₃	46
14	AgSbF₆ (15)	PhCH₃	32
15	AgSbF₆ (15)	CH₃CN	ND
16	AgSbF₆ (15)	THF	ND
17	AgSbF₆ (10)	CH₂Cl₂	85
18	AgSbF₆ (20)	CH₂Cl₂	88
19^c	AgSbF₆ (15)	CH₂Cl₂	57
20^d	AgSbF₆ (15)	CH₂Cl₂	ND
21^e	AgSbF₆ (15)	CH₂Cl₂	88
22^f	AgSbF₆ (15)	CH₂Cl₂	74
23^g	AgSbF₆ (15)	CH₂Cl₂	87
24^h	AgSbF₆ (15)	CH₂Cl₂	85
25ⁱ	AgSbF₆ (15)	CH₂Cl₂	79

银催化环状Morita-Baylis-Hillman醇及其类似物与芳基乙烯的顺式[5＋2]环加成反应研究

cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)

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