有机化学 ›› 2022, Vol. 42 ›› Issue (6): 1722-1734.DOI: 10.6023/cjoc202112023 上一篇 下一篇
研究论文
王兴a, 宋倩倩a, 陈续玲b, 李鹏飞b,*(), 齐昀坤a,*(), 李文军a,*()
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:
基金资助:
Xing Wanga, Qianqian Songa, Xuling Chenb, Pengfei Lib(), Yunkun Qia(), Wenjun Lia()
Received:
2021-12-18
Revised:
2022-02-28
Published:
2022-03-08
Contact:
Pengfei Li, Yunkun Qi, Wenjun Li
About author:
Supported by:
文章分享
报道了在手性磷酸作用下6-吲哚甲醇原位生成6-亚甲基-6H-吲哚, 继而与异噁唑-5(4H)-酮发生不对称1,8-共轭加成反应. 该反应实现了异噁唑-5(4H)-酮的对映选择性N-烷基化, 以70%~83%的产率和61%~96%的对映选择性得到共轭加成产物.
王兴, 宋倩倩, 陈续玲, 李鹏飞, 齐昀坤, 李文军. 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[J]. 有机化学, 2022, 42(6): 1722-1734.
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.
Entry | Catalyst | Solvent | Yieldb/% | eec/% |
---|---|---|---|---|
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 |
13d | CPA-5 | Xylenes | 3aa, 81 | 96 |
14e | CPA-5 | Xylenes | 3aa, 74 | 92 |
15f | CPA-5 | Xylenes | 3aa, 83 | 94 |
Entry | Catalyst | Solvent | Yieldb/% | eec/% |
---|---|---|---|---|
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 |
13d | CPA-5 | Xylenes | 3aa, 81 | 96 |
14e | CPA-5 | Xylenes | 3aa, 74 | 92 |
15f | CPA-5 | Xylenes | 3aa, 83 | 94 |
Entrya | Ar | R1 | Yieldb/% | eec/% |
---|---|---|---|---|
1 | 4-MeOC4H6 | Ph | 3aa, 81 | 96 |
2d | 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 |
7d | 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 |
Entrya | Ar | R1 | Yieldb/% | eec/% |
---|---|---|---|---|
1 | 4-MeOC4H6 | Ph | 3aa, 81 | 96 |
2d | 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 |
7d | 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 |
Entrya | R2 | R3 | 3, Yieldb/% | eec/% |
---|---|---|---|---|
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 |
13d | Ph | H | 3an, 75 | 63 |
14 | Me | Ph | 3ao, 81 | 61 |
15e | Et | Ph | 3ap, 72 | 70 |
16 | Ph | Ph | 3aq, 82 | 84 |
Entrya | R2 | R3 | 3, Yieldb/% | eec/% |
---|---|---|---|---|
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 |
13d | Ph | H | 3an, 75 | 63 |
14 | Me | Ph | 3ao, 81 | 61 |
15e | Et | Ph | 3ap, 72 | 70 |
16 | Ph | Ph | 3aq, 82 | 84 |
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