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

[21] Enantioselective synthesis of 3-hydroxy oxindoles by ytterbium-catalysed decarboxylative addition of β-ketoacids to isatins
Duan, Zhiqiang
Han, Jianlin
Qian, Ping
Zhang, Zirui
Wang, Yi
Pan, Yi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (38) : 6456 - 6459
[22] An enantioselective cascade reaction between α, β-unsaturated aldehydes and malonic half-thioesters: a rapid access to chiral δ-lactones
Ren, Qiao
Sun, Shaofa
Huang, Jiayao
Li, Wenjun
Wu, Minghu
Guo, Haibing
Wang, Jian
CHEMICAL COMMUNICATIONS, 2014, 50 (46) : 6137 - 6140
[23] Gaining Insight Into Reactivity Differences Between Malonic Acid Half Thioesters (MAHT) and Malonic Acid Half Oxyesters (MAHO)
Bew, Sean P.
Stephenson, G. Richard
Rouden, Jacques
Godemert, Jeremey
Seylani, Haseena
Martinez-Lozano, Luis A.
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (19) : 4557 - 4569
[24] Organocatalytic Enantioselective Morita-Baylis-Hillman Reaction of Maleimides with Isatins
Chauhan, Pankaj
Chimni, Swapandeep Singh
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (07) : 586 - 592
[25] Organocatalytic Asymmetric Decarboxylative Addition of -Ketoacids to Methyleneindolinones Derivatives
Kumari, Anita
Kaur, Jasneet
Bhardwaj, Vimal K.
Chimni, Swapandeep Singh
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4081 - 4088
[26] Organocatalytic enantioselective conjugate addition to alkynones
Bella, M
Jorgensen, KA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) : 5672 - 5673
[27] Enantioselective organocatalytic amine conjugate addition
Chen, Young K.
Yoshida, Masanori
MacMillan, David W. C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) : 9328 - 9329
[28] Enantioselective organocatalytic amine conjugate addition
Chen, Young K.
Yoshida, Masanori
MacMillan, David W. C.
Journal of the American Chemical Society, 2006, 128 (29): : 9328 - 9329
[29] Enantioselective Organocatalytic Rearrangement of α-Acyloxy-β-keto Sulfides to α-Acyloxy Thioesters
Capitta, Francesca
Frongia, Angelo
Piras, Pier Paolo
Pitzanti, Patrizia
Secci, Francesco
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) : 2955 - 2960
[30] Decarboxylative Claisen Condensations with Substituted Malonic Acid Half Oxyesters
Xavier, Tania
Tran, Parvine
Gautreau, Apolline
Le Gall, Erwan
Presset, Marc
SYNTHESIS-STUTTGART, 2023, 55 (04): : 598 - 608

← 1 2 3 4 5 →