Enantioselective decarboxylative protonation and deuteration of β-ketocarboxylic acids

被引：10

作者：

Mizutani, Haruna ^{[1
]}

Kawanishi, Ryouta ^{[1
]}

Shibatomi, Kazutaka ^{[1
]}

机构：

[1] Toyohashi Univ Technol, Dept Appl Chem & Life Sci, 1-1 Hibarigaaka,Tempaku Cho, Toyohashi, Aichi 4418580, Japan

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 54期

关键词：

DERIVATIVES; ENANTIOMERS;

D O I：

10.1039/d1cc01610e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective decarboxylative protonation of tetralone-derived beta-ketocarboxylic acids was achieved with up to 89% enantiomeric excess (ee)-in the presence of a chiral primary amine catalyst. Furthermore, this method was applied to enantioselective deuteration to afford the corresponding alpha-deuterioketones with up to 88% ee.

引用

页码：6676 / 6679

页数：4

共 50 条

[41] Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling
Gao, Bao
Xie, Yinjun
Shen, Zhiqiang
Yang, Lei
Huang, Hanmin
ORGANIC LETTERS, 2015, 17 (20) : 4968 - 4971
[42] Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams
Behenna, Douglas C.
Liu, Yiyang
Yurino, Taiga
Kim, Jimin
White, David E.
Virgil, Scott C.
Stoltz, Brian M.
NATURE CHEMISTRY, 2012, 4 (02) : 130 - 133
[43] Enantioselective Synthesis of Spiroimines by Asymmetric Decarboxylative Alkylation/Isomerization/[3+2]-Cycloaddition Reaction of Azidoalkenes
Rambla, Matt
Duroure, Leslie
Chabaud, Laurent
Guillou, Catherine
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (34) : 7716 - 7720
[44] Photoredox-Catalyzed Decarboxylative Cross-Coupling of α-Amino Acids with Nitrones
Li, Heng-Hui
Li, Jia-Qi
Zheng, Xiao
Huang, Pei-Qiang
ORGANIC LETTERS, 2021, 23 (03) : 876 - 880
[45] Synthesis of Substituted Stilbenes via Direct Decarboxylative Coupling of Cinnamic Acids with Arylboronic Acids under Palladium Catalysis
Yamashita, Mana
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
CHEMISTRY LETTERS, 2010, 39 (01) : 68 - 69
[46] Visible light photocatalytic decarboxylative monofluoroalkenylation of α-amino acids with gem-difluoroalkenes
Li, Jingjing
Lefebvre, Quentin
Yang, Haijun
Zhao, Yufen
Fu, Hua
CHEMICAL COMMUNICATIONS, 2017, 53 (74) : 10299 - 10302
[47] Synthesis of Amino Acids by Base-Enhanced Photoredox Decarboxylative Alkylation of Aldimines
Wang, Jiancheng
Shao, Ziyan
Tan, Kai
Tang, Rui
Zhou, Qingli
Xu, Min
Li, Ya-Min
Shen, Yuehai
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15) : 9944 - 9954
[48] Engaging α-Fluorocarboxylic Acids Directly in Decarboxylative C-C Bond Formation
Wang, Hongyu
Liu, Chen-Fei
Song, Zhihui
Yuan, Mingbin
Ho, Yee Ann
Gutierrez, Osvaldo
Koh, Ming Joo
ACS CATALYSIS, 2020, 10 (07) : 4451 - 4459
[49] Stereoselective Palladium-Catalyzed Decarboxylative γ-Arylation of Acyclic β,γ-Unsaturated Carboxylic Acids
Scheipers, Ina
Koch, Eva
Studer, Armido
ORGANIC LETTERS, 2017, 19 (07) : 1741 - 1743
[50] Copper-Catalyzed Decarboxylative Phosphorylation of Coumarin-3-carboxylic Acids
Ghoghari, Rajnikant N.
Patel, Anant R.
Patel, Parth P.
Chikhalia, Kishor H.
SYNLETT, 2025,

← 1 2 3 4 5 →