Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes

doi:10.6023/cjoc202006036

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 348-356.DOI: 10.6023/cjoc202006036 Previous Articles Next Articles

Special Issue: 有机硅化学虚拟合辑

Article

二苯基八氢吲哚醇硅醚催化α,β-不饱和醛不对称[3+3] 氮杂环化反应合成苯并呋喃衍生物

温慧玲^a, 罗年华^a, 欧阳露^a, 罗人仕^a^,^*()

a 赣南医学院药学院江西赣州 341000

收稿日期:2020-06-19 修回日期:2020-08-09 发布日期:2020-08-27
通讯作者: 罗人仕
作者简介:
* Corresponding author. E-mail: luorenshi2010@163.com
基金资助:
国家自然科学基金(21962004); 国家自然科学基金(21562004); 江西省自然科学基金(20192BAB203004); 江西省教育厅(GJJ190829); 赣南医学院(QD201832); 赣南医学院(QD201816); 赣南医学院(YJ202027)

Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes

Huiling Wen^a, Nianhua Luo^a, Lu Ouyang^a, Renshi Luo^a^,^*()

a School of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000

Received:2020-06-19 Revised:2020-08-09 Published:2020-08-27
Contact: Renshi Luo
Supported by:
the National Natural Science Foundation of China(21962004); the National Natural Science Foundation of China(21562004); the Jiangxi Provincial Department of Science and Technology(20192BAB203004); the Foundation of Jiangxi Provincial Department of Education(GJJ190829); Gannan Medical University(QD201832); Gannan Medical University(QD201816); Gannan Medical University(YJ202027)

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Abstract

A highly enantioselective [3+3] aza-cyclization of α, β-unsaturated aldehydes with 3-aminobenzofuran promoted by diphenylperhydroindolinol silyl ether has been described, which afforded benzofuran derivatives in high yields (up to 93%), diastereoselectivities ( dr>20∶1) and enantioselectivities (86%~>99% ee). This method also enabled to obtain benzofuran derivatives in gram scale-up.

Key words: diphenylperhydroindolinol silyl ether, [3+3] aza-cyclizationαβ-unsaturated aldehydes, 3-aminobenzofuran

Cite this article

Huiling Wen, Nianhua Luo, Lu Ouyang, Renshi Luo. Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 348-356.

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Fig. & Tab. 7

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Entry	R ¹	R ²	t/h	Yield ^b /% ( 3)	ee ^c /%
1	H	Ph	5	93 ( 3aa)	98
2	H	4-ClC ₆H ₄	14	92 ( 3ab)	>99
3	H	3-ClC ₆H ₄	72	90 ( 3ac)	91
4	H	2-ClC ₆H ₄	17	89 ( 3ad)	97
5	H	4-NO ₂C ₆H ₄	8	90 ( 3ae)	>99
6	H	2-NO ₂C ₆H ₄	12	87 ( 3af)	95
7	H	4-BrC ₆H ₄	14	93 ( 3ag)	>99
8	H	4-FC ₆H ₄	13	93 ( 3ah)	>99
9	H	4-CH ₃C ₆H ₄	24	92 ( 3ai)	96
10	H	4-OCH ₃C ₆H ₄	18	93 ( 3aj)	97
11	H	2-OCH ₃C ₆H ₄	24	92 ( 3ak)	91
12	H	2,6-F ₂C ₆H ₃	18	93 ( 3al)	>99
13	6-Cl	4-BrC ₆H ₄	15	92 ( 3ba)	>99
14	6-Cl	4-ClC ₆H ₄	15	91 ( 3bb)	>99
15	6-Cl	4-FC ₆H ₄	13	92 ( 3bc)	>99
16	6-Cl	4-CH ₃C ₆H ₄	18	92 ( 3bd)	>99
17	6-Cl	2-OCH ₃C ₆H ₄	24	93 ( 3be)	>99
18	6-Cl	4-OCH ₃C ₆H ₄	18	91 ( 3bf)	>99
19	6-Cl	2-ClC ₆H ₄	15	90 ( 3bg)	>99
20	6-Cl	4-NO ₂C ₆H ₄	13	90 ( 3bh)	>99
21	6-Cl	2-NO ₂C ₆H ₄	18	92 ( 3bi)	>99
22	6-Cl	3-ClC ₆H ₄	72	92 ( 3bj)	>99
23	6-Cl	2,6-F ₂C ₆H ₃	18	93 ( 3bk)	>99
24	6-Cl	Ph	8	93 ( 3bl)	97
25	H	Propyl	72	43 ( 3bm)	86 ^d

Entry	R ¹	R ²	t/h	Yield ^b /% ( 3)	ee ^c /%
1	H	Ph	5	93 ( 3aa)	98
2	H	4-ClC ₆H ₄	14	92 ( 3ab)	>99
3	H	3-ClC ₆H ₄	72	90 ( 3ac)	91
4	H	2-ClC ₆H ₄	17	89 ( 3ad)	97
5	H	4-NO ₂C ₆H ₄	8	90 ( 3ae)	>99
6	H	2-NO ₂C ₆H ₄	12	87 ( 3af)	95
7	H	4-BrC ₆H ₄	14	93 ( 3ag)	>99
8	H	4-FC ₆H ₄	13	93 ( 3ah)	>99
9	H	4-CH ₃C ₆H ₄	24	92 ( 3ai)	96
10	H	4-OCH ₃C ₆H ₄	18	93 ( 3aj)	97
11	H	2-OCH ₃C ₆H ₄	24	92 ( 3ak)	91
12	H	2,6-F ₂C ₆H ₃	18	93 ( 3al)	>99
13	6-Cl	4-BrC ₆H ₄	15	92 ( 3ba)	>99
14	6-Cl	4-ClC ₆H ₄	15	91 ( 3bb)	>99
15	6-Cl	4-FC ₆H ₄	13	92 ( 3bc)	>99
16	6-Cl	4-CH ₃C ₆H ₄	18	92 ( 3bd)	>99
17	6-Cl	2-OCH ₃C ₆H ₄	24	93 ( 3be)	>99
18	6-Cl	4-OCH ₃C ₆H ₄	18	91 ( 3bf)	>99
19	6-Cl	2-ClC ₆H ₄	15	90 ( 3bg)	>99
20	6-Cl	4-NO ₂C ₆H ₄	13	90 ( 3bh)	>99
21	6-Cl	2-NO ₂C ₆H ₄	18	92 ( 3bi)	>99
22	6-Cl	3-ClC ₆H ₄	72	92 ( 3bj)	>99
23	6-Cl	2,6-F ₂C ₆H ₃	18	93 ( 3bk)	>99
24	6-Cl	Ph	8	93 ( 3bl)	97
25	H	Propyl	72	43 ( 3bm)	86 ^d

二苯基八氢吲哚醇硅醚催化α,β-不饱和醛不对称[3+3] 氮杂环化反应合成苯并呋喃衍生物

Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes

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Entry	Cat.	t/h	Yield ^b /%	ee ^c /%
1	Cat-1	24	85	82
2	Cat-2	18	84	18
3	Cat-3	36	73	38
4	Cat-4	36	71	10
5	Cat-5	36	75	50
6	Cat-6	48	75	71

Entry	Solvent	t/h	Yield ^b /%	ee ^c /%
1	CH ₂Cl ₂	28	89	74
2	Toluene	24	91	71
3	Hexane	24	91	60
4	Acetone	24	92	70
5	THF	28	85	51
6	Et ₂O	24	81	51
7	MeOH	28	88	61
8	MeCN	24	95	82
9 ^d	MeCN	16	86	94
10 ^e	MeCN	18	87	93

Entry	Cat-1/mol%	Additive	t/h	Yield ^b /%	ee ^c /%
1	20	DNBA	48	83	93
2	20	BA	15	86	83
3	20	PNBA	5	95	98
4 ^d	20	PNBA	6	91	98
5 ^e	20	PNBA	5	93	98
6 ^f	20	PNBA	8	91	93
7	10	PNBA	32	63	97
8	5	PNBA	120	31	97