有机化学 ›› 2021, Vol. 41 ›› Issue (10): 4039-4049.DOI: 10.6023/cjoc202105055 上一篇 下一篇
所属专题： 南开大学化学学科创立100周年
研究论文
赵敏a, 李霏a, 程益政b, 王有名a, 周正洪a,*(
)
收稿日期:2021-05-31
修回日期:2021-06-22
发布日期:2021-07-05
通讯作者:
周正洪
Min Zhaoa, Fei Lia, Yizheng Chengb, Youming Wanga, Zhenghong Zhoua()
Received:2021-05-31
Revised:2021-06-22
Published:2021-07-05
Contact:
Zhenghong Zhou
文章分享
发展了一种有机催化的邻羟基苯基取代对甲亚基苯醌和β-氧代酰基吡唑之间的不对称[4+2]环化反应, 为光学活性3,4-二氢香豆素衍生物的获取提供了有效途径. 在衍生自奎宁的手性双功能方酰胺催化下, 一系列邻羟基苯基取代对甲亚基苯醌和β-氧代酰基吡唑可以在温和的条件下顺利地发生反应, 以高产率和优秀的非对映及对映选择性得到相应的多取代3,4-二氢香豆素衍生物.
赵敏, 李霏, 程益政, 王有名, 周正洪. 有机催化邻羟基官能化的对甲亚基苯醌和β-氧代酰基吡唑的不对称[4+2]环化合成光学活性3,4-二氢香豆素衍生物[J]. 有机化学, 2021, 41(10): 4039-4049.
Min Zhao, Fei Li, Yizheng Cheng, Youming Wang, Zhenghong Zhou. Optically Active 3,4-Dihydrocoumarins via Organocatalyzed Asymmetric [4+2] Annulation of ortho-Hydroxyl Functionalized p-Quinone Methides with β-Keto Acylpyrazoles[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4039-4049.
| Entry | Catalyst | Time/h | Yieldb/% | Drc | eed/% |
|---|---|---|---|---|---|
| 1 | I | 8 | 81 | >19/1 | 77 |
| 2 | IIa | 12 | 89 | >19/1 | 67 |
| 3 | IIb | 12 | 85 | >19/1 | 70 |
| 4 | III | 8 | 90 | >19/1 | –89 |
| 5 | IV | 8 | 80 | >19/1 | 80 |
| 6 | Va | 12 | 84 | >19/1 | 78 |
| 7 | Vb | 12 | 83 | >19/1 | 76 |
| 8 | VIa | 8 | 89 | >19/1 | –77 |
| 9 | VIb | 8 | 86 | >19/1 | –79 |
| 10 | VIc | 8 | 79 | >19/1 | –83 |
| 11 | VII | 8 | 90 | >19/1 | –94 |
| Entry | Catalyst | Time/h | Yieldb/% | Drc | eed/% |
|---|---|---|---|---|---|
| 1 | I | 8 | 81 | >19/1 | 77 |
| 2 | IIa | 12 | 89 | >19/1 | 67 |
| 3 | IIb | 12 | 85 | >19/1 | 70 |
| 4 | III | 8 | 90 | >19/1 | –89 |
| 5 | IV | 8 | 80 | >19/1 | 80 |
| 6 | Va | 12 | 84 | >19/1 | 78 |
| 7 | Vb | 12 | 83 | >19/1 | 76 |
| 8 | VIa | 8 | 89 | >19/1 | –77 |
| 9 | VIb | 8 | 86 | >19/1 | –79 |
| 10 | VIc | 8 | 79 | >19/1 | –83 |
| 11 | VII | 8 | 90 | >19/1 | –94 |
| Entry | Solvent | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | CH2Cl2 | 8 | 84 | >19/1 | 94 |
| 2 | CHCl3 | 8 | 80 | >19/1 | 88 |
| 3 | Cl(CH2)2Cl | 7 | 78 | >19/1 | 90 |
| 4 | PhCl | 6 | 79 | >19/1 | 84 |
| 5 | PhF | 6 | 75 | >19/1 | 80 |
| 6 | PhCH3 | 6 | 76 | >19/1 | 76 |
| 7 | EtOAc | 48 | 45 | >19/1 | 70 |
| 8 | CH3CN | 48 | 43 | >19/1 | 81 |
| 9e | CH2Cl2 | 36 | 80 | >19/1 | 93 |
| 10f | CH2Cl2 | 8 | 85 | >19/1 | 51 |
| 11g | CH2Cl2 | 5 | 80 | >19/1 | 88 |
| 12h | CH2Cl2 | 12 | 83 | >19/1 | 85 |
| Entry | Solvent | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | CH2Cl2 | 8 | 84 | >19/1 | 94 |
| 2 | CHCl3 | 8 | 80 | >19/1 | 88 |
| 3 | Cl(CH2)2Cl | 7 | 78 | >19/1 | 90 |
| 4 | PhCl | 6 | 79 | >19/1 | 84 |
| 5 | PhF | 6 | 75 | >19/1 | 80 |
| 6 | PhCH3 | 6 | 76 | >19/1 | 76 |
| 7 | EtOAc | 48 | 45 | >19/1 | 70 |
| 8 | CH3CN | 48 | 43 | >19/1 | 81 |
| 9e | CH2Cl2 | 36 | 80 | >19/1 | 93 |
| 10f | CH2Cl2 | 8 | 85 | >19/1 | 51 |
| 11g | CH2Cl2 | 5 | 80 | >19/1 | 88 |
| 12h | CH2Cl2 | 12 | 83 | >19/1 | 85 |
| Entry | 3 (R, Ar) | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | 3aa (H, Ph) | 8 | 84 | >19/1 | 94 |
| 2 | 3ba (4-Me, Ph) | 48 | 80 | >19/1 | 92 |
| 3 | 3ca (5-Me, Ph) | 48 | 81 | >19/1 | 97 |
| 4 | 3da (3-MeO, Ph) | 32 | 80 | >19/1 | 96 |
| 5 | 3ea (4-MeO, Ph) | 8 | 85 | >19/1 | 93 |
| 6 | 3fa (5-MeO, Ph) | 32 | 84 | >19/1 | 93 |
| 7 | 3ga (5-F, Ph) | 5 | 86 | >19/1 | 95 |
| 8 | 3ha (4-Cl, Ph) | 8 | 82 | >19/1 | 97 |
| 9 | 3ia (5-Cl, Ph) | 8 | 82 | >19/1 | 86 |
| 10 | 3ja (4-Br, Ph) | 8 | 77 | >19/1 | 98 |
| 11 | 3ka (5-Br, Ph) | 8 | 68 | >19/1 | 95 |
| 12 | 3ab (H, 4-MeC6H4) | 8 | 79 | >19/1 | 92 |
| 13 | 3ac (H, 3-MeC6H4) | 8 | 78 | >19/1 | 93 |
| 14 | 3ad (H, 2-MeC6H4) | 8 | 85 | >19/1 | 90 |
| 15 | 3ae (H, 4-MeOC6H4) | 8 | 85 | >19/1 | 91 |
| 16 | 3af (H, 3,4-(MeO)2C6H3) | 8 | 66 | >19/1 | 86 |
| 17 | 3ag (H, 4-FC6H4) | 8 | 83 | >19/1 | 93 |
| 18 | 3ah (H, 3-ClC6H4) | 8 | 90 | >19/1 | 96 |
| 19 | 3ai (H, 4-BrC6H4) | 8 | 81 | >19/1 | 94 |
| 20 | 3aj (H, 3-BrC6H4) | 8 | 80 | >19/1 | 95 |
| 21 | 3ak (H, 2-Naphthyl) | 8 | 89 | >19/1 | 87 |
| 22 | 3al (H, 2-Thienyl) | 8 | 90 | >19/1 | 93 |
| Entry | 3 (R, Ar) | Time/h | Yieldb/% | drc | eed/% |
|---|---|---|---|---|---|
| 1 | 3aa (H, Ph) | 8 | 84 | >19/1 | 94 |
| 2 | 3ba (4-Me, Ph) | 48 | 80 | >19/1 | 92 |
| 3 | 3ca (5-Me, Ph) | 48 | 81 | >19/1 | 97 |
| 4 | 3da (3-MeO, Ph) | 32 | 80 | >19/1 | 96 |
| 5 | 3ea (4-MeO, Ph) | 8 | 85 | >19/1 | 93 |
| 6 | 3fa (5-MeO, Ph) | 32 | 84 | >19/1 | 93 |
| 7 | 3ga (5-F, Ph) | 5 | 86 | >19/1 | 95 |
| 8 | 3ha (4-Cl, Ph) | 8 | 82 | >19/1 | 97 |
| 9 | 3ia (5-Cl, Ph) | 8 | 82 | >19/1 | 86 |
| 10 | 3ja (4-Br, Ph) | 8 | 77 | >19/1 | 98 |
| 11 | 3ka (5-Br, Ph) | 8 | 68 | >19/1 | 95 |
| 12 | 3ab (H, 4-MeC6H4) | 8 | 79 | >19/1 | 92 |
| 13 | 3ac (H, 3-MeC6H4) | 8 | 78 | >19/1 | 93 |
| 14 | 3ad (H, 2-MeC6H4) | 8 | 85 | >19/1 | 90 |
| 15 | 3ae (H, 4-MeOC6H4) | 8 | 85 | >19/1 | 91 |
| 16 | 3af (H, 3,4-(MeO)2C6H3) | 8 | 66 | >19/1 | 86 |
| 17 | 3ag (H, 4-FC6H4) | 8 | 83 | >19/1 | 93 |
| 18 | 3ah (H, 3-ClC6H4) | 8 | 90 | >19/1 | 96 |
| 19 | 3ai (H, 4-BrC6H4) | 8 | 81 | >19/1 | 94 |
| 20 | 3aj (H, 3-BrC6H4) | 8 | 80 | >19/1 | 95 |
| 21 | 3ak (H, 2-Naphthyl) | 8 | 89 | >19/1 | 87 |
| 22 | 3al (H, 2-Thienyl) | 8 | 90 | >19/1 | 93 |
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CCDC-2086168 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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