Organocatalytic Enantioselective Decarboxylative Addition of Malonic Acids Half Thioesters to Isatins

被引：101

作者：

Hara, Noriyuki ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Funahashi, Yasuhiro ^{[1
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 16期

关键词：

aldol reaction; decarboxylative addition; enantioselectivity; organic catalysis; ASYMMETRIC ALDOL CONDENSATION; 1ST TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SQUARAMIDE DERIVATIVES; (R)-CONVOLUTAMYDINE; SULFONYLIMINES; ACETALDEHYDE; ALKALOIDS; KETONES;

D O I：

10.1002/adsc.201100410

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The organocatalytic enantioselective decarboxylative addition of malonic acids half thioesters to isatins using a squaramide catalyst afforded the products with high enantioselectivity. These products are key intermediates in the synthesis of 3-substituted 3-hydroxy-2-oxindole derivatives. The first enantioselective synthesis of (-)-flustraminol B has been accomplished.

引用

页码：2976 / 2980

页数：5

共 50 条

[31] Enantioselective decarboxylative chlorination of β-ketocarboxylic acids
Shibatomi, Kazutaka
Kitahara, Kazumasa
Sasaki, Nozomi
Kawasaki, Yohei
Fujisawa, Ikuhide
Iwasa, Seiji
NATURE COMMUNICATIONS, 2017, 8
[32] Enantioselective decarboxylative chlorination of β-ketocarboxylic acids
Kazutaka Shibatomi
Kazumasa Kitahara
Nozomi Sasaki
Yohei Kawasaki
Ikuhide Fujisawa
Seiji Iwasa
Nature Communications, 8
[33] Asymmetric Malonic and Acetoacetic Acid Syntheses - A Century of Enantioselective Decarboxylative Protonations
Blanchet, Jerome
Baudoux, Jerome
Amere, Mukkanti
Lasne, Marie-Claire
Rouden, Jacques
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (33) : 5493 - 5506
[34] Chiral Squaramide-Catalyzed Enantioselective Decarboxylative Addition of -Keto Acids to Isatin Imines
Kaur, Jasneet
Kumari, Anita
Bhardwaj, Vimal K.
Chimni, Swapandeep Singh
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) : 1725 - 1734
[35] Organocatalysis for Enantioselective Decarboxylative Nucleophilic Addition Reactions
Yasukawa, Naoki
Nakamura, Shuichi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (35)
[36] Organocatalytic enantioselective decarboxylative protonation of α-alkyl-α-aryl malonate monoesters
Guo, Cong-Ying
Chen, Jia-Zheng
Liu, Wen-Ting
Mei, Hao
Meng, Jie
Chen, Jian-Ping
CHEMICAL COMMUNICATIONS, 2024, 60 (28) : 3854 - 3857
[37] Organocatalytic asymmetric decarboxylative cyanomethylation of isatins using L-proline derived bifunctional thiourea
Gajulapalli, V. Pratap Reddy
Vinayagam, Poopathy
Kesavan, Venkitasamy
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (24) : 4186 - 4191
[38] Enantioselective organocatalytic conjugate addition of α-aminoketone to nitroolefins
Belot, Sebastien
Sulzer-Mosse, Sarah
Kehrli, Stefan
Alexakis, Alexandre
CHEMICAL COMMUNICATIONS, 2008, (39) : 4694 - 4696
[39] Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Nitrodienes
Belot, Sebastien
Massaro, Assunta
Tenti, Alice
Mordini, Alessandro
Alexakis, Alexandre
ORGANIC LETTERS, 2008, 10 (20) : 4557 - 4560
[40] Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines
Liu, Xiangyuan
Liu, Yang
Chai, Guobi
Qiao, Baokun
Zhao, Xiaowei
Jiang, Zhiyong
ORGANIC LETTERS, 2018, 20 (19) : 6298 - 6301

← 1 2 3 4 5 →