Asymmetric Aza Friedel–Crafts Reaction of 3,4-Dihydroisoquinolines with 1‑Naphthols Catalyzed by Chiral Phosphoric Acids
An efficient chiral phosphoric acid-catalyzed asymmetric aza Friedel–Crafts reaction of 3,4-dihydroisoquinolines and 1-naphthols is described. The reaction provides a general method for the synthesis of diverse chiral tetrahydroisoquinoline with 1-naphthol substituents at the C1-position in excellen...
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| Veröffentlicht in: | Journal of organic chemistry 2024-11, Vol.89 (21), p.15553-15558 |
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| container_end_page | 15558 |
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| container_issue | 21 |
| container_start_page | 15553 |
| container_title | Journal of organic chemistry |
| container_volume | 89 |
| creator | Zhang, Ye Gan, Qiaoyu Zhang, Xujin Dai, Xiandong Meng, Fanhua Gao, Zhenhua Si, Yujun Guo, Yongbiao |
| description | An efficient chiral phosphoric acid-catalyzed asymmetric aza Friedel–Crafts reaction of 3,4-dihydroisoquinolines and 1-naphthols is described. The reaction provides a general method for the synthesis of diverse chiral tetrahydroisoquinoline with 1-naphthol substituents at the C1-position in excellent yields and enantioselectivities. Based on the conducted mechanistic experiments, a plausible catalytic mechanism was proposed. Moreover, the practicability of the reaction is successfully demonstrated by its application on a gram scale. |
| doi_str_mv | 10.1021/acs.joc.4c01617 |
| format | Article |
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Org. Chem</addtitle><description>An efficient chiral phosphoric acid-catalyzed asymmetric aza Friedel–Crafts reaction of 3,4-dihydroisoquinolines and 1-naphthols is described. The reaction provides a general method for the synthesis of diverse chiral tetrahydroisoquinoline with 1-naphthol substituents at the C1-position in excellent yields and enantioselectivities. Based on the conducted mechanistic experiments, a plausible catalytic mechanism was proposed. 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Org. Chem</addtitle><date>2024-11-01</date><risdate>2024</risdate><volume>89</volume><issue>21</issue><spage>15553</spage><epage>15558</epage><pages>15553-15558</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>An efficient chiral phosphoric acid-catalyzed asymmetric aza Friedel–Crafts reaction of 3,4-dihydroisoquinolines and 1-naphthols is described. The reaction provides a general method for the synthesis of diverse chiral tetrahydroisoquinoline with 1-naphthol substituents at the C1-position in excellent yields and enantioselectivities. Based on the conducted mechanistic experiments, a plausible catalytic mechanism was proposed. 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| title | Asymmetric Aza Friedel–Crafts Reaction of 3,4-Dihydroisoquinolines with 1‑Naphthols Catalyzed by Chiral Phosphoric Acids |
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