Enantioselective Synthesis of an All-Carbon Quaternary Stereocenter by Chiral Br?nsted Acid-Catalyzed Friedel-Crafts-Type Reaction between Pyrroles and 3-Indolylmethanols

被引：5

作者：

Uchikura, Tatsuhiro ^{[1
]}

Sanchez-Sordo, Irene ^{[1
]}

Yoshimura, Tatsuhiko ^{[1
]}

Makino, Yudai ^{[1
]}

Osakabe, Hiroto ^{[1
]}

Akiyama, Takahiko ^{[1
]}

机构：

[1] Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 12期

关键词：

BRONSTED ACID; NATURAL-PRODUCTS; INDOLE; ALKYLATION; CONSTRUCTION;

D O I：

10.1021/acs.joc.2c02633

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a chiral phosphoric acid-catalyzed enantioselective Friedel-Crafts alkylation reaction between pyrroles and indolylmethanols. Wide substrate scope was observed, and a chiral all-carbon quaternary center was constructed at the 3 position of indoles in high yields with high to excellent enantioselectivities (up to 99% ee).

引用

页码：7774 / 7783

页数：10

共 14 条

[1] Chiral Calcium Phosphate Catalyzed Enantioselective Synthesis of All-Carbon Quaternary Center by Friedel-Crafts Alkylation Reaction of Pyrroles and Trifluoromethylated Nitrostyrenes
Uchikura, Tatsuhiro
Yokohama, Sosuke
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SYNTHESIS-STUTTGART, 2022, 54 (17): : 3793 - 3800
[2] Asymmetric Synthesis of β-Indolyl Cyclopentanones and Cyclopentylamides with an All-Carbon Quaternary Stereocenter via Chiral Phosphoric Acid Catalyzed Friedel-Crafts Alkylation Reactions
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Rajkumar, Subramani
Wu, Weihu
Huang, Ziyu
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ORGANIC LETTERS, 2019, 21 (10) : 3563 - 3567
[3] Synthesis of Chiral Bis(3-indolyl)methanes Bearing a Trifluoromethylated All-Carbon Quaternary Stereocenter via Nickel-Catalyzed Asymmetric Friedel-Crafts Alkylation Reaction
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Gong, Jun-Fang
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JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15) : 9525 - 9537
[4] Stereoselective construction of all-carbon quaternary center by means of chiral phosphoric acid: highly enantioselective Friedel-Crafts reaction of indoles with β,β-disubstituted nitroalkenes
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[5] Chiral Phosphoric Acid-Catalyzed Asymmetric Aza-Friedel-Crafts Reaction of Indoles with Cyclic N-Acylketimines: Enantioselective Synthesis of Trifluoromethyldihydroquinazolines
Zhang, Ke-Feng
Nie, Jing
Guo, Ran
Zheng, Yan
Ma, Jun-An
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3497 - 3502
[6] Enatioselective Synthesis of Tetrahydrocarbazoles via Chiral Phosphoric Acid Promoted Domino Friedel-Crafts-type Reaction of Indole-3-butanal with Indoles
Yu, Shuowen
Chen, Hui
Xu, Xiaoying
Yuan, Weicheng
Zhang, Xiaomei
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (03) : 619 - 631
[7] Chiral Bronsted acid-catalyzed Friedel-Crafts reaction of 3-indolylsulfamidates with indoles: Synthesis of enantioenriched bisindolylmethane sulfamates
Kim, Yerin
Lee, Jiseon
Jung, Junyang
Kim, Sung-Gon
TETRAHEDRON LETTERS, 2019, 60 (25) : 1625 - 1630
[8] Chiral phosphoric acid-catalyzed enantioselective synthesis of functionalized pyrrolinones containing a geminal diamine core via an aza-Friedel-Crafts reaction of newly developed pyrrolinone ketimines
Zhang, Tong
Wang, Zhen-Hua
Li, Yong
Zhao, Jian-Qiang
You, Yong
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ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (05) : 1437 - 1443
[9] Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of naphthols and electron-rich phenols with 2-aryl-3H-indol-3-ones
Ma, Tao
He, Yonghui
Qiao, Xiu-Xiu
Zou, Chang-Peng
Wu, Xi-Xi
Li, Ganpeng
Zhao, Xiao-Jing
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (03) : 489 - 493
[10] Catalytic Asymmetric Synthesis of 3,3′-Diaryloxindoles as Triarylmethanes with a Chiral All-Carbon Quaternary Center: Phase-Transfer-Catalyzed SNAr Reaction
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Tokuda, Takashi
Yamamoto, Kenichiro
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (24) : 6220 - 6223

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