Cu(i)-Catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1,3-O-transposition reaction

被引：12

作者：

Zhang, Changyuan ^{[1
]}

Chen, Lianfen ^{[1
]}

Chen, Kai ^{[1
]}

Wang, Chuntao ^{[1
]}

Xu, Zurong ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Zhu, Shifa ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 16期

基金：

中国博士后科学基金;

关键词：

ANTI-MARKOVNIKOV ADDITION; CARBOXYLIC-ACIDS; TERMINAL ALKYNES; RUTHENIUM COMPLEXES; RAPID ACCESS; CATALYSIS; ETHERS; REARRANGEMENT; CYCLIZATION; CARBENES;

D O I：

10.1039/c8qo00664d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Cu(i)-catalyzed stereoselective synthesis of trisubstituted Z-enol esters via interrupting the 1,3-O-transposition process is reported. This method provided a convenient approach to highly functionalized Z-enol esters with mild reaction conditions and wide substrate scope.

引用

页码：2510 / 2514

页数：5

共 50 条

[21] Regiospecific and stereoselective synthesis of (E)- and (Z)-2-phosphino-1-alkenyl boronates via Cu-catalyzed hydroboration of alkynylphosphines
Song, Liubing
Ma, Xufeng
Xu, Sheng
Shi, Min
Zhang, Jun
NEW JOURNAL OF CHEMISTRY, 2018, 42 (11) : 8342 - 8345
[22] (Z)-γ-Alkylidenebutenolide Synthesis through Au(I)-Catalyzed 1,3-Acyloxy Migration and the Carbonyl-Ene Reaction
Amin, Pathan Mosim
Cui, Qi
Wang, Shaozhong
Yu, Zhi-Xiang
ORGANIC LETTERS, 2021, 23 (15) : 5669 - 5673
[23] Stereoselective synthesis of (Z)-enynes via Pd(II)/CuI(I)-catalyzed cross-coupling reaction of bis-vinylic tellurides with 1-alkynes
Zeni, G
Menezes, PH
Moro, AV
Braga, AL
Silveira, CC
Stefani, WA
SYNLETT, 2001, (09) : 1473 - 1475
[24] Synthesis of functionalized α-CF3-α-aminophosphonates via Cu(I)-catalyzed 1,3-dipolar cycloaddition
Vorobyeva, Dana V.
Karimova, Natalya M.
Vasilyeva, Tamara P.
Osipov, Sergey N.
Shchetnikov, Grigory T.
Odinets, Irina L.
Roeschenthaler, Gerd-V.
JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (03) : 378 - 383
[25] A convenient synthesis of 1,4,5-trisubstituted 1,2,3-triazoles via 1,3-dipolar cycloaddition/coupling of alkynes, phenylboronic acids, and sodium azide catalyzed by Cu(I)/Cu(II)
Yang, Dong
Fu, Na
Liu, Zenglu
Li, Ying
Chen, Baohua
SYNLETT, 2007, (02) : 278 - 282
[26] STEREOSELECTIVE SYNTHESIS OF (Z,E)-2-BROMO-1,3-DIENES VIA THE PALLADIUM (O) CATALYZED CROSS COUPLING REACTIONS OF 1,1-DIBROMOOLEFINS AND VINYLBORONIC ACIDS
ROUSH, WR
MORIARTY, KJ
BROWN, BB
TETRAHEDRON LETTERS, 1990, 31 (45) : 6509 - 6512
[27] NOVEL RUTHENIUM-CATALYZED SYNTHESIS OF 1,3-DIOXOLAN-4-ONES FROM ALPHA-HYDROXY ACIDS AND TERMINAL ALKYNES VIA ENOL ESTERS
NEVEUX, M
SEILLER, B
HAGEDORN, F
BRUNEAU, C
DIXNEUF, PH
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 451 (1-2) : 133 - 138
[28] Kinetic separation methodology for the stereoselective synthesis of (E)- and (Z)-α-fluoro-α,β-unsaturated esters via the palladium-catalyzed carboalkoxylation of 1-bromo-1-fluoroalkenes
Xu, JJ
Burton, DJ
ORGANIC LETTERS, 2002, 4 (05) : 831 - 833
[29] Stereoselective synthesis of conjugated alkadienes via the palladium-catalyzed coupling reaction of (Z)- or (E)-alkenylboranes with (Z)- or (E)-2-halo-1-(alkylseleno)ethenes
Yang, DY
Huang, X
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 543 (1-2) : 165 - 169
[30] Site-selective synthesis of 1,3-dioxin-3-ones via a gold(i) catalyzed cascade reaction
An, Juzeng
Pedrazzani, Riccardo
Monari, Magda
Marin-Luna, Marta
Silva Lopez, Carlos
Bandini, Marco
CHEMICAL COMMUNICATIONS, 2020, 56 (56) : 7734 - 7737

← 1 2 3 4 5 →