Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative

doi:10.6023/cjoc202009023

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1187-1192.DOI: 10.6023/cjoc202009023 Previous Articles Next Articles

ARTICLES

金鸡纳硅醚衍生物有机催化吲哚与靛红的不对称Friedel-Crafts反应

张俊伟^a^,^b, 吴昊^a^,^b, 张伟鑫^a, 王黎明^a^,^*(), 金瑛^a^,^*()

a 吉林医药学院药学院吉林吉林 132013
b 延边大学药学院吉林延吉 133000

收稿日期:2020-09-09 修回日期:2020-10-19 发布日期:2020-11-12
通讯作者: 王黎明, 金瑛
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21102055); 吉林省自然科学基金(20190201077JC); 吉林省卫生厅技术创新项目(2020J074); 国家大学生创新创业训练计划(201913706058)

Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative

Junwei Zhang^a^,^b, Hao Wu^a^,^b, Weixin Zhang^a, Liming Wang^a^,^*(), Ying Jin^a^,^*()

a Department of Pharmacy, Jilin Medical University, Jilin, Jilin 132013
b Department of Pharmacy, Yanbian University, Yanjin, Jilin 133000

Received:2020-09-09 Revised:2020-10-19 Published:2020-11-12
Contact: Liming Wang, Ying Jin
About author:
* Corresponding authors. E-mail: jinying2288@163.com;
13630635312@163.com
† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(21102055); Natural Science Foundation of Jilin Province(20190201077JC); Technology Innovation Project of the Health Commission of Jilin Province(2020J074); National Students? Program for Innovation and Entrepreneurship Training(201913706058)

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Abstract

A series of cinchona alkaloid silyl ether derivatives have been used to catalyze the enantioselective Friedel-Crafts reaction of indoles with isatins. The resulting 3-hydroxy-2-oxindoles were obtained in good yields (78%~96%) with high enantioselectivities (up to 99% ee). The catalyst type and the substrate scope were broadened in this methodology.

Key words: cinchona alkaloid silyl ether, organocatalysis, isatin, indole, enantioselective Friedel-Crafts reaction

Cite this article

Junwei Zhang, Hao Wu, Weixin Zhang, Liming Wang, Ying Jin. Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1187-1192.

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References 10

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Entry	Catalyst	Yield^b/%	ee^c/%	Conf.^d
1	1a	86	38	S
2	1b	90	82	S
3	1c	92	89	S
4	1d	88	87	R
5	1e	84	75	R
6	1f	87	71	R

Entry	Catalyst	Yield^b/%	ee^c/%	Conf.^d
1	1a	86	38	S
2	1b	90	82	S
3	1c	92	89	S
4	1d	88	87	R
5	1e	84	75	R
6	1f	87	71	R

Entry	Product	R¹	R²	R³	Yield^b/%	ee^c/%
1	4a	H	H	H	92	94
2	4b	H	5-F	H	78	86
3	4c	H	5-Cl	H	85	90
4	4d	H	5-Br	H	90	90
5	4e	H	5-Me	H	83	90
6	4f	H	7-F	H	92	90
7	4g	H	H	Bn	81	93
8	4h	5-Br	H	H	95	90
9	4i	5-Br	5-F	H	96	90
10	4j	5-Br	7-F	H	88	85
11	4k	5-OMe	H	Bn	86	90
12	4l	5-Me	H	Bn	92	90
13	4m	6-Cl	H	H	85	93
14	4n	6-Cl	5-F	H	87	88
15	4o	6-Cl	5-Me	H	88	84
16	4p	6-Cl	7-F	H	92	99
17	4q	6-Cl	H	Bn	87	96

Entry	Product	R¹	R²	R³	Yield^b/%	ee^c/%
1	4a	H	H	H	92	94
2	4b	H	5-F	H	78	86
3	4c	H	5-Cl	H	85	90
4	4d	H	5-Br	H	90	90
5	4e	H	5-Me	H	83	90
6	4f	H	7-F	H	92	90
7	4g	H	H	Bn	81	93
8	4h	5-Br	H	H	95	90
9	4i	5-Br	5-F	H	96	90
10	4j	5-Br	7-F	H	88	85
11	4k	5-OMe	H	Bn	86	90
12	4l	5-Me	H	Bn	92	90
13	4m	6-Cl	H	H	85	93
14	4n	6-Cl	5-F	H	87	88
15	4o	6-Cl	5-Me	H	88	84
16	4p	6-Cl	7-F	H	92	99
17	4q	6-Cl	H	Bn	87	96

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金鸡纳硅醚衍生物有机催化吲哚与靛红的不对称Friedel-Crafts反应

Enantioselective Friedel-Crafts Reaction of Indoles with Isatins Catalyzed by Cinchona Alkaloid Silyl Ether Derivative

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Entry	Solvent	Temp./℃	Cat./ mol%	Yield^b/%	ee^c/%
1	THF	r.t.	10	92	89
2	Et₂O	r.t.	10	84	17
3	CH₂Cl₂	r.t.	10	60	10
4	PhMe	r.t.	10	78	34
5	1,4-dioxane	r.t.	10	76	59
6^d	1,4-dioxane	r.t.	20	81	92
7	THF	r.t.	20	91	83
8	THF	r.t.	5	83	70
9	THF	0	10	86	58
10^e	THF	r.t.	10	92	94