Efficient synthesis of γ-oxo carboxylic esters and isotope-labeled 5-aminolevulinic acid (5-ALA) by Pd(OAc)2/phosphonium tetrafluoroborates catalyzed Fukuyama coupling reaction

被引：2

作者：

Aoyama, Hiroshi ^{[1
]}

Iizuka, Yusuke ^{[1
]}

Kawanishi, Ryouta ^{[2
]}

Shibatomi, Kazutaka ^{[2
,3
]}

Arakawa, Yuki ^{[2
]}

Tsuji, Hideto ^{[2
]}

Hirose, Yuu ^{[2
]}

Mishima, Masaki ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, 1432 1 Horinouchi, Hachioji, Tokyo 1920392, Japan

[2] Toyohashi Univ Technol, Dept Appl Chem & Life Sci, 1 1 Hibarigaoka, Tempaku cho, Toyohashi, Aichi 4418580, Japan

[3] Toyohashi Univ Technol, Inst Res Next Generat Semicond & Sensing Sci, 1 1 Hibarigaoka, Tempaku cho, Toyohashi, Aichi 4418580, Japan

来源：

TETRAHEDRON LETTERS | 2023年 / 123卷

关键词：

Fukuyama coupling reaction; y-Oxo carboxylic ester; Phosphonium tetrafluoroborate; Palladium catalyst; 5-Aminolevulinic acid; DELTA-AMINOLEVULINIC-ACID; OXIDATIVE ADDITION; BIOSYNTHESIS; PALLADIUM; HALIDES; SALTS; HEME; ARYL; ALA;

D O I：

10.1016/j.tetlet.2023.154570

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd(OAc)2/phosphonium tetrafluoroborates efficiently catalyzed Fukuyama coupling reaction with p-tolyl thioesters and 3-ethoxy-3-oxopropylzinc bromide which provide y-oxo carboxylic esters under mild con-ditions. Pd(OAc)2/PCy3 & BULL;HBF4 is the most effective catalyst and provides a direct method for synthesizing functionalized y-oxo esters with high efficiency from readily accessible carboxylic acids as starting mate-rials. By utilizing the optimized conditions, isotope-labeled 5-aminolevulinic acid ((15N)-5-ALA) was effi-ciently synthesized.& COPY; 2023 Elsevier Ltd. All rights reserved.

引用

页数：5

共 4 条

[1] Highly efficient phosphine-free Pd(OAc)2-catalyzed Fukuyama coupling reaction:: Synthesis of a key intermediate for (+)-biotin under low catalyst loading
Mori, Y
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SYNLETT, 2005, (14) : 2233 - 2235
[2] Efficient synthesis of 2,6-disubstituted-5-hydroxy-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid ethyl esters
Murphy, Douglas E.
Dragovich, Peter S.
Ayida, Benjamin K.
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TETRAHEDRON LETTERS, 2008, 49 (05) : 811 - 815
[3] Efficient synthesis of 4-(2′-alkenyl)-2,5-dihydrofurans and 5,6-dihydro-2H-pyrans via the Pd-catalyzed cyclizative coupling reaction of 2,3-or 3,4-allenols with allylic halides
Ma, SM
Gao, WZ
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17): : 6104 - 6112
[4] An efficient synthesis of carbon-14-labeled 6-[2-(dimethylamino)ethyl]-14-(1-ethylpropyl)-5,6,7,8-tetrahydroindolo [2,1-α] [2,5]benzodiazocine-11-carboxylic acid using Curtius rearrangement reaction as a key step
Zhang, Andy Shiqiang
Ho, Jonathan Z.
Braun, Matthew P.
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2011, 54 (03): : 163 - 167

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