Electroreductive Ring-Opening Carboxylation of 1,3-Oxazolidin-2-ones with CO2 for Accessing β-Amino Acids

被引：3

作者：

Tao, Li ^{[1
]}

Liu, Xiao-Fei ^{[1
]}

Ren, Bai-Hao ^{[1
]}

Wang, He ^{[1
]}

Sun, Hui-Qin ^{[1
]}

Zhang, Ke ^{[1
]}

Teng, Yong-Qiang ^{[1
]}

Ren, Wei-Min ^{[1
]}

Lu, Xiao-Bing ^{[1
]}

Zhang, Wen-Zhen ^{[1
]}

机构：

[1] Dalian Univ Technol, Frontiers Sci Ctr Smart Mat, State Key Lab Fine Chem, Dalian 116024, Liaoning, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 02期

基金：

中国国家自然科学基金;

关键词：

ELECTROCARBOXYLATION;

D O I：

10.1021/acs.orglett.3c04007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrocarboxylation of the C(sp(3))-O bond in 1,3-oxazolidin-2-ones with CO2 to achieve beta-amino acids is developed. The C-O bond in substrates can be selectively cleaved via the single electron transfer on the surface of a cathode or through a CO2 center dot (-) intermediate under additive-free conditions. A great diversity of beta-amino acids can be obtained in a moderate to excellent yield and readily converted to various biologically active compounds.

引用

页码：542 / 546

页数：5

共 50 条

[21] Stereoselective Diels-Alder reactions of 3-phosphonopropenoyl derivatives of 1,3-oxazolidin-2-ones
Cheng, Eileen W. C.
Mandalia, Reena T.
Motevalli, Majid
Mothia, Begum
Patanwadia, Yashvant
Wyatt, Peter B.
TETRAHEDRON, 2006, 62 (52) : 12398 - 12407
[22] Diastereoselective conjugate additions to t-leucine-derived N-enoyl 1,3-oxazolidin-2-ones
Schneider, C
Reese, O
SYNTHESIS-STUTTGART, 2000, (12): : 1689 - 1694
[23] Visible-Light Photoredox-Catalyzed Ring-Opening Carboxylation of Cyclic Oxime Esters with CO2
Jiang, Yuan-Xu
Chen, Liang
Ran, Chuan-Kun
Song, Lei
Zhang, Wei
Liao, Li-Li
Yu, Da-Gang
CHEMSUSCHEM, 2020, 13 (23) : 6312 - 6317
[24] Activation of aldehydes by exocyclic iridium(I)-η4:π2-diene complexes derived from 1,3-oxazolidin-2-ones
Padilla, Rosa
Salazar-Pereda, Veronica
Mendoza-Espinosa, Daniel
Vasquez-Perez, Jose M.
Andrade-Lopez, Noemi
Tamariz, Joaquin
Alvarado-Rodriguez, Jose G.
Cruz-Borbolla, Julian
DALTON TRANSACTIONS, 2016, 45 (42) : 16878 - 16888
[25] N-substituted 5-aryl-1,3-oxazolidin-2-ones from arylethylene oxides
Wrobel, Z.
Bobin, M.
Karczewski, R.
POLISH JOURNAL OF CHEMISTRY, 2006, 80 (06) : 907 - 912
[26] Cationic and anionic ring-opening polymerization in supercritical CO2
Mingotaud, AF
Dargelas, F
Cansell, F
MACROMOLECULAR SYMPOSIA, 2000, 153 : 77 - 86
[27] 1,2-OXAZOLIDINES .5. SPIRO AND CONDENSED BIHETEROCYCLIC ISOMERS FROM NITRONES AND 1,3-OXAZOLIDIN-2-ONES
AVERSA, MC
CUM, G
GIANNETT.PD
ROMEO, G
UCCELLA, N
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (02): : 209 - 215
[28] N-SUBSTITUTED 5-{[2-(VINYLOXY)ETHOXY]METHYL}-1,3-OXAZOLIDIN-2-ONES - NEW ANTIBACTERIAL AGENTS
Belovezhets, L. A.
Lobanova, N. A.
Sadykov, E. Kh.
Stankevich, V. K.
IZVESTIYA VUZOV-PRIKLADNAYA KHIMIYA I BIOTEKHNOLOGIYA, 2016, 6 (03): : 21 - 25
[29] Enantioselective Synthesis of Spirooxindolopyrrolizidines via Catalytic 1,3-dipolar Cycloaddition of Azomethine Ylides and 3-(2-Alkenoyl)-1,3-oxazolidin-2-ones
Taghizadeh, Mohammad Javad
Javidan, Abdollah
Jadidi, Khosrow
JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2015, 59 (03): : 205 - 208
[30] SYNTHESIS AND SPECTRAL BEHAVIOR OF 5-METHYL-3-PHENYL-1,3-OXAZOLIDIN-2-ONES USING NMR
NISHIYAMA, T
MATSUI, S
YAMADA, F
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (05) : 1427 - 1429

← 1 2 3 4 5 →