Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

doi:10.6023/cjoc202112023

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1722-1734.DOI: 10.6023/cjoc202112023 Previous Articles Next Articles

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有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应

王兴^a, 宋倩倩^a, 陈续玲^b, 李鹏飞^b^,^*(), 齐昀坤^a^,^*(), 李文军^a^,^*()

a 青岛大学药学院山东青岛 266073
b 南方科技大学理学院格拉布斯研究院化学系广东省催化化学重点实验室广东深圳 518055

收稿日期:2021-12-18 修回日期:2022-02-28 发布日期:2022-03-08
通讯作者: 李鹏飞, 齐昀坤, 李文军
作者简介:
† 共同第一作者
基金资助:
山东省自然科学基金(ZR2021MB026); 山东省泰山学者(tsqn201812047); 深圳市科委创新(20200925151614002); 广东省催化化学重点实验室(2020B121201002)

Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

Xing Wang^a, Qianqian Song^a, Xuling Chen^b, Pengfei Li^b(), Yunkun Qi^a(), Wenjun Li^a()

a School of Pharmacy, Qingdao University, Qingdao, Shandong 266073
b Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, South University of Science and Technology of China, Shenzhen, Guangzhou 518055

Received:2021-12-18 Revised:2022-02-28 Published:2022-03-08
Contact: Pengfei Li, Yunkun Qi, Wenjun Li
About author:
† These authors contributed equally to this work
Supported by:
Natural Science Foundation of Shandong Province(ZR2021MB026); Special Funds of the Taishan Scholar Program of Shandong Province(tsqn201812047); Shenzhen Innovation of Science and Technology Commission(20200925151614002); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

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Abstract

A chiral phosphoric acid catalyzed aza-1,8-conjugate addition of isoxazol-5(4H)-ones to 6-methylene-6H-indoles formed in situ from 6-indolylmethanols has been developed for the first time. Notably, the remote stereocontrolled 1,8-addition of isoxazol-5(4H)-ones was featured by N-selectivity, affording aza-adducts in 70%~83% yields with 61%~96% ee.

Key words: asymmetric organocatalysis, conjugate addition, isoxazol-5(4H)-ones, 6-methylene-6H-indole

Cite this article

Xing Wang, Qianqian Song, Xuling Chen, Pengfei Li, Yunkun Qi, Wenjun Li. Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1722-1734.

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Entry	Catalyst	Solvent	Yield^b/%	ee^c/%
1	CPA-1	CH₂Cl₂	3aa, 75	≈28
2	CPA-2	CH₂Cl₂	3aa, 74	≈53
3	CPA-3	CH₂Cl₂	3aa, 62	≈66
4	CPA-4	CH₂Cl₂	3aa, 57	≈68
5	CPA-5	CH₂Cl₂	3aa, 77	88
6	CPA-6	CH₂Cl₂	3aa, 49	48
7	CPA-5	CHCl₃	3aa, 80	68
8	CPA-5	THF	3aa, 68	43
9	CPA-5	Et₂O	3aa, 65	49
10	CPA-5	Toluene	3aa, 77	76
11	CPA-5	PhCF₃	3aa, 69	90
12	CPA-5	Xylenes	3aa, 70	96
13^d	CPA-5	Xylenes	3aa, 81	96
14^e	CPA-5	Xylenes	3aa, 74	92
15^f	CPA-5	Xylenes	3aa, 83	94

Entry	Catalyst	Solvent	Yield^b/%	ee^c/%
1	CPA-1	CH₂Cl₂	3aa, 75	≈28
2	CPA-2	CH₂Cl₂	3aa, 74	≈53
3	CPA-3	CH₂Cl₂	3aa, 62	≈66
4	CPA-4	CH₂Cl₂	3aa, 57	≈68
5	CPA-5	CH₂Cl₂	3aa, 77	88
6	CPA-6	CH₂Cl₂	3aa, 49	48
7	CPA-5	CHCl₃	3aa, 80	68
8	CPA-5	THF	3aa, 68	43
9	CPA-5	Et₂O	3aa, 65	49
10	CPA-5	Toluene	3aa, 77	76
11	CPA-5	PhCF₃	3aa, 69	90
12	CPA-5	Xylenes	3aa, 70	96
13^d	CPA-5	Xylenes	3aa, 81	96
14^e	CPA-5	Xylenes	3aa, 74	92
15^f	CPA-5	Xylenes	3aa, 83	94

Entry^a	Ar	R¹	Yield^b/%	ee^c/%
1	4-MeOC₄H₆	Ph	3aa, 81	96
2^d	4-MeC₄H₆	Ph	3ba, 76	96
3	4-FC₄H₆	Ph	3ca, 77	96
4	3-MeOC₄H₆	Ph	3da, 70	80
5	3-ClC₄H₆	Ph	3ea, 70	84
6	2-MeC₄H₆	Ph	3fa, 79	67
7^d	Ph	Ph	3ga, 75	77
8	4-MeOC₄H₆	4-MeOC₄H₆	3ha, 81	94
9	4-MeOC₄H₆	2-MeOC₄H₆	3ia, 81	92
10	4-MeOC₄H₆	2-Naphthyl	3ja, 74	95
11	4-MeOC₄H₆	H	3ka, 70	75
12	4-MeOC₄H₆	Me	3la, 79	65

Entry^a	Ar	R¹	Yield^b/%	ee^c/%
1	4-MeOC₄H₆	Ph	3aa, 81	96
2^d	4-MeC₄H₆	Ph	3ba, 76	96
3	4-FC₄H₆	Ph	3ca, 77	96
4	3-MeOC₄H₆	Ph	3da, 70	80
5	3-ClC₄H₆	Ph	3ea, 70	84
6	2-MeC₄H₆	Ph	3fa, 79	67
7^d	Ph	Ph	3ga, 75	77
8	4-MeOC₄H₆	4-MeOC₄H₆	3ha, 81	94
9	4-MeOC₄H₆	2-MeOC₄H₆	3ia, 81	92
10	4-MeOC₄H₆	2-Naphthyl	3ja, 74	95
11	4-MeOC₄H₆	H	3ka, 70	75
12	4-MeOC₄H₆	Me	3la, 79	65

有机催化远程立体控制6-亚甲基-6H-吲哚与异噁唑-5(4H)-酮的氮杂1,8-共轭加成反应

Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

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Entry^a	R²	R³	3, Yield^b/%	ee^c/%
1	Ph	4-MeOC₄H₆	3ab, 82	92
2	Ph	4-ClC₄H₆	3ac, 70	89
3	Ph	4-BrC₄H₆	3ad, 79	94
4	Ph	4-NO₂C₄H₆	3ae, 74	90
5	Ph	3-MeC₄H₆	3af, 79	96
6	Ph	3-ClC₄H₆	3ag, 79	92
7	Ph	3-BrC₄H₆	3ah, 79	96
8	Ph	2-MeC₄H₆	3ai, 77	94
9	Ph	2-BrC₄H₆	3aj, 77	86
10	Ph	2-Naphthyl	3ak, 83	90
11	Ph	1-Naphthyl	3al, 79	96
12	Ph	2-Furyl	3am, 80	66
13^d	Ph	H	3an, 75	63
14	Me	Ph	3ao, 81	61
15^e	Et	Ph	3ap, 72	70
16	Ph	Ph	3aq, 82	84

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