Practical Stereoselective Synthesis of C3-Spirooxindole- and C2-Spiropseudoindoxyl-Pyrrolidines via Organocatalyzed Pictet-Spengler Reaction/Oxidative Rearrangement Sequence

被引：8

作者：

Kondo, Masaru ^{[1
]}

Matsuyama, Naoki ^{[1
]}

Aye, Tin Z. ^{[1
]}

Mattan, Irshad ^{[1
]}

Sato, Tomoyuki ^{[2
]}

Makita, Yoshinori ^{[2
,3
]}

Ishibashi, Masami ^{[2
]}

Arai, Midori A. ^{[3
]}

Takizawa, Shinobu ^{[1
,4
]}

Sasai, Hiroaki ^{[1
,4
]}

机构：

[1] Osaka Univ, Inst Sci & Ind Res ISIR, Ibaraki, Osaka 5670047, Japan

[2] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan

[3] Keio Univ, Fac Sci & Technol, Kohoku Ku, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

[4] Osaka Univ, Artificial Intelligence Res Ctr, ISIR, Suita, Osaka, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 10期

关键词：

Squaramide catalyst; Spiro compound; One-pot synthesis; Green oxidant; Wnt signaling inhibitory activity;

D O I：

10.1002/adsc.202001472

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A stereoselective synthetic route to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines was accomplished by an enantioselective organocatalyzed Pictet-Spengler reaction of tryptamines and isotryptamines followed by a diastereoselective oxidative rearrangement using eco-friendly oxidants (i. e., NaOCl . 5H(2)O and Oxone (R)). This sequential reaction enables rapid access to chiral C3-spirooxindole- and C2-spiropseudoindoxyl-pyrrolidines in a one-pot process. A Wnt signaling inhibitory assay of the prepared enantioenriched spiro compounds demonstrated that they exhibited moderate activities.

引用

页码：2648 / 2663

页数：16

共 2 条

[1] Practical Synthesis of Functionalized Chromeno[3,4-c]pyridine Derivatives via a CuCl2-Catalyzed Tandem Reaction of the Blaise Reaction Intermediates and 3-Cyanocoumarins
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Chen, Zhiwei
SYNLETT, 2018, 29 (07) : 959 - 963
[2] Synthesis of 2,4,5-Trisubstituted Oxazoles from Copper-Mediated Benzylic sp3 C-H Aerobic Oxidative Annulation of Ketones and Amines via a Cascade Reaction
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JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02) : 1227 - 1234

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