[読みたい論文] フロー系でケトンからエポキシドを合成します

Viewed: 14:41:32 in January 25, 2020

Posted: December 25, 2019

Continuous Flow Synthesis of Terminal Epoxides from Ketones Using in Situ Generated Bromomethyl Lithium (Keutz, Timo von; Cantillo, David; Kappe, C. Oliver)
Org. Lett. 2019, 21 (24), 10094−10098.

Keywords: Johnson–Corey–Chaykovsky reaction; fluconazole; 読みたい論文シリーズ; 有機化学; ブログ


Prof. Kappe、有機反応を様々な装置で試している印象がありますが、この論文でもマイクロリアクターでの反応を報告しています。

取り扱っている反応はケトンとブロモメチルリチウムの反応によるエポキシド合成。ブロモメチルリチウムはフロー系中でジブロモメタンとメチルリチウムから作っています。2つの経路からの合流で反応を起こさせているわけですが、1つの経路にはケトンとジブロモメタン、もう一つの経路にはメチルリチウムとなっており、あらかじめ調製したブロモメチルリチウムを流し込んで着るわけではないようです。

このフロー系での反応、低温で行われており、反応に使用する化合物の融点や溶解度を「フラスコ反応より」気にしなくてはならないわけで、その辺りに関する様々な工夫がSupporting Informationに書かれています。本文はもちろんですが、Supporting Informationも読む価値ありです。市販のメチルリチウムはそのまま使えない、などなど。

Corey–Chaykovsky反応に対する利点はそうだよねとは思いますが(これフロー系でできる反応なのか?)、ケトンとブロモメチルリチウムの反応をこの論文に記載のフロー反応とフラスコ反応とでどのくらいの差があるのか、本文中に書かれているような気がしますので、読みたい論文に追加です。

この記事を書いた人
「牧岡ふうふ堂」オーナー。博士(工学)。
酒都圏在住。
某地方の国立系工業大学でアシスタントをしていました。 専門は有機反応・金属錯体(主に希土類)・π共役系。
twitterアカウントは@makiokafufudo(お仕事用)、@ymakioka(個人用)です。

 

きょうのどうぶつ

ここの画像を使用しています。

しばらく姿を見せていなかった朝青龍。生きていた。

 

計算終わりました

 

あわせてどうぞ

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注目のWebコンテンツ

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[Org. Lett. 2019, 21, 10081−10084]
Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst
(Hoshi, Takayuki; Ota, Eisuke; Inokuma, Yasuhide; Yamaguchi, Junichiro)
Tag: H, as, Sn, Alk

[Org. Lett. 2019, 21, 10099−10101]
Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael–Aldol–Acetalization Cascade
(Kawamoto, Misaki; Sato, Shuntaro; Enomoto, Masaru; Ogura, Yusuke; Kuwahara, Shigefumi)
Tag: Sn, O, DMK, MA, DHA, Ph, ACE

[Org. Lett. 2019, 21, 10130−10133]
Zinc-Catalyzed Synthesis of Acylsilanes Using Carboxylic Acids and a Silylborane in the Presence of Pivalic Anhydride
(Tatsumi, Kenta; Tanabe, Sae; Tsuji, Yasushi; Fujihara, Tetsuaki)
Tag: Zn, COOH, SiH4

ポリオキソ金属酸  
[J. Am. Chem. Soc. 2019, 141, 19550−19554]
Controlled Assembly Synthesis of Atomically Precise Ultrastable Silver Nanoclusters with Polyoxometalates
(Yonesato, Kentaro; Ito, Hiroyasu; Itakura, Hiroyuki; Yokogawa, Daisuke; Kikuchi, Takashi; Mizuno, Noritaka; Yamaguchi, Kazuya; Suzuki, Kosuke)
Tag: at., Ag, NC, CT, Sn, VL, POM, CTB, e-

[J. Am. Chem. Soc. 2019, 141, 19565−19569]
Transcription of Chirality from Metal–Organic Framework to Polythiophene
(Kitao, Takashi; Nagasaka, Yujiro; Karasawa, Masanobu; Eguchi, Toshiki; Kimizuka, Nobuo; Ishii, Kazuyuki; Yamada, Teppei; Uemura, Takashi)
Tag: PT, TP, TPH, PTH, CD

[J. Am. Chem. Soc. 2019, 141, 19570−19574]
Amphiprotism-Coupled Near-Infrared Emission in Extended Pyrazinacenes Containing Seven Linearly Fused Pyrazine Units
(Richards, Gary J.; Cador, Aël; Yamada, Shinji; Middleton, Anna; Webre, Whitney A.; Labuta, Jan; Karr, Paul A.; Ariga, Katsuhiko; D’Souza, Francis; Kahlal, Samia; Halet, Jean-François; Hill, Jonathan P.)
Tag: lb, N, PL, PLQY, QY, em, Sn, ABS, NIR, LQY, e-, IR

[J. Am. Chem. Soc. 2019, 141, 19611−19615]
Carboxylation of Benzylic and Aliphatic C–H Bonds with CO2 Induced by Light/Ketone/Nickel
(Ishida, Naoki; Masuda, Yusuke; Imamura, Yuuya; Yamazaki, Katsushi; Murakami, Masahiro)
Tag: Ni, AA, C, K, Sn, Bn, Hx, HC, PhMe, tBuOK, COOH, CHX, cy-hex, KTB, Ph, TolH, Hex, AcOH, C7H12O2, CyH

自己集合  
[J. Am. Chem. Soc. 2019, 141, 19669−19676]
Navigated Self-Assembly of a Pd2L4 Cage by Modulation of an Energy Landscape under Kinetic Control
(Tateishi, Tomoki; Takahashi, Satoshi; Okazawa, Atsushi; Martí-Centelles, Vicente; Wang, Jianzhu; Kojima, Tatsuo; Lusby, Paul J.; Sato, Hirofumi; Hiraoka, Shuichi)
Tag: Sn, rds, NpH, thermodn., decompd., decomp., SA

膜タンパク質  
[J. Am. Chem. Soc. 2019, 141, 19677−19687]
1,3,5-Triazine-Cored Maltoside Amphiphiles for Membrane Protein Extraction and Stabilization
(Ghani, Lubna; Munk, Chastine F.; Zhang, Xiang; Katsube, Satoshi; Du, Yang; Cecchetti, Cristina; Huang, Weijiao; Bae, Hyoung Eun; Saouros, Savvas; Ehsan, Muhammad; Guan, Lan; Liu, Xiangyu; Loland, Claus J.; Kobilka, Brian K.; Byrne, Bernadette; Chae, Pil Seok)
Tag: lb, PCR, DEA, Deanol, CH3CH2OH, CC, GPCR, NH2, MP, GPGR, Alk, EtOH

ナノ粒子  
[J. Am. Chem. Soc. 2019, 141, 19754−19764]
Three-Stage Evolution from Nonscalable to Scalable Optical Properties of Thiolate-Protected Gold Nanoclusters
(Zhou, Meng; Higaki, Tatsuya; Li, Yingwei; Zeng, Chenjie; Li, Qi; Sfeir, Matthew Y.; Jin, Rongchao)
Tag: NC, Au, Sn, TA, QC, ABS, NP

[J. Am. Chem. Soc. 2019, 141, 19807−19816]
Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues
(Hayakawa, Sakiho; Kawasaki, Ayumi; Hong, Yongseok; Uraguchi, Daisuke; Ooi, Takashi; Kim, Dongho; Akutagawa, Tomoyuki; Fukui, Norihito; Shinokubo, Hiroshi)
Tag: PI, PDI, EF, H, N, as, EEF, PY, Per, PBI, e-, HB, HB, Alk, Ar

[J. Am. Chem. Soc. 2019, 141, 19859−19869]
Isolation and Study of Ruthenium–Cobalt Oxo Cubanes Bearing a High-Valent, Terminal RuV–Oxo with Significant Oxyl Radical Character
(Amtawong, Jaruwan; Balcells, David; Wilcoxen, Jarett; Handford, Rex C.; Biggins, Naomi; Nguyen, Andy I.; Britt, R. David; Tilley, T. Don)
Tag: Trt, Res, OAc, A, R, Pyr, Sn, tBu, t-Bu, Bu, pyr, oxidn., expt., Py, NBO, e-, Cat

[Energy Fuels 2019, 33, 12679−12684]
Stable Boron-Modified ZSM-22 Zeolite Catalyst for Selective Production of Propylene from Methanol
(Jamil, Anas K.; Nishitoba, Toshiyuki; Yamani, Zain H.; Yokoi, Toshiyuki; Muraza, Oki)
Tag: TPD, B, Sn, EM, FT, CH3CH2OH, MAS, pyr, ZL, CH3OH, NH3, morphol., morph., Py, TEM, e-, SEM, IR, Cat, EtOH

[Energy Fuels 2019, 33, 12865−12870]
Impact of Mass Transfer in the Carbon/Carbonate-Packed Bed on the Power Output of a Press-Type Direct Carbon Fuel Cell
(Watanabe, Hirotatsu; Shimada, Takashi; Nakanouchi, Minori; Hanamura, Katsunori)
Tag: DCFC, IS, C, Sn, FC, curr.

[Energy Fuels 2019, 33, 12894−12904]
Hydroperoxide Formation and Thermal Oxidation of Methyl tert-Butyl Ether Oxidation at Low Temperature
(Zhang, Qiang; Kumasaki, Mieko; Liu, Xiongmin; Ren, Fan; Nishiwaki, Yosuke; Wang, Bo; Matsue, Satoshi)
Tag: FTIR, ER, LC, Et, MR, Sn, FT, tBu, t-Bu, Bu, HPO, Bum, oxidn., DSC, MRS, decompn., expt., ETBE, MTBE, Me, MCPVT, NMR, IR, MS, Ea

[ACS Synth. Biol. 2019, 8, 2679−2689]
Switching the Ligand Specificity of the Biosensor XylS from meta to para-Toluic Acid through Directed Evolution Exploiting a Dual Selection System
(Ogawa, Yuki; Katsuyama, Yohei; Ueno, Kento; Ohnishi, Yasuo)
Tag: TAT, AA, Sn, BZA, BzOH, CAP, operon

[ACS Synth. Biol. 2019, 8, 2701−2709]
Single-Stage Astaxanthin Production Enhances the Nonmevalonate Pathway and Photosynthetic Central Metabolism in Synechococcus sp. PCC 7002
(Hasunuma, Tomohisa; Takaki, Ayako; Matsuda, Mami; Kato, Yuichi; Vavricka, Christopher J.; Kondo, Akihiko)
Tag: Zea, HL, C, CN, Sn, CAR, AXT, curr., DCW

[ACS Chem. Biol. 2019, 14, 2553−2556]
Subtle Control of Carbon Chain Length in Polyunsaturated Fatty Acid Synthases
(Naka, Mai; Ikeuchi, Kenshin; Hayashi, Shohei; Satoh, Yasuharu; Ogasawara, Yasushi; Dairi, Tohru)
Tag: AA, CLF

[ACS Chem. Biol. 2019, 14, 2576−2584]
The ARH and Macrodomain Families of α-ADP-ribose-acceptor Hydrolases Catalyze α-NAD+ Hydrolysis
(Stevens, Linda A.; Kato, Jiro; Kasamatsu, Atsushi; Oda, Hirotake; Lee, Duck-Yeon; Moss, Joel)
Tag: R, Arg, FG, Rib, Cat

[ACS Chem. Biol. 2019, 14, 2606−2615]
Dual Inhibitors of 8-Oxoguanine Surveillance by OGG1 and NUDT1
(Tahara, Yu-ki; Kietrys, Anna M.; Hebenbrock, Marian; Lee, Yujeong; Wilson, David L.; Kool, Eric T.)
Tag: lb, OS, G, Gua, Sn, expt.

鉄  
[ACS Chem. Biol. 2019, 14, 2729−2736]
Histidine-Mediated Intramolecular Electrostatic Repulsion for Controlling pH-Dependent Protein–Protein Interaction
(Watanabe, Hideki; Yoshida, Chuya; Ooishi, Ayako; Nakai, Yasuto; Ueda, Momoko; Isobe, Yutaka; Honda, Shinya)
Tag: MI, Fe, IgG, Ig, H, Lys, K, Sn, Ab, His, H, thermodn., curr., HB

[ACS Chem. Biol. 2019, 14, 2822−2832]
Development of Small Molecule Chimeras That Recruit AhR E3 Ligase to Target Proteins
(Ohoka, Nobumichi; Tsuji, Genichiro; Shoda, Takuji; Fujisato, Takuma; Kurihara, Masaaki; Demizu, Yosuke; Naito, Mikihiko)
Tag: lb, AhR, C, Ub, Sn, HC, UPP, CRABP, RA, Ar

[ACS Chem. Biol. 2019, 14, 2851−2858]
Synthetic Chemical Probes That Dissect Vitamin D Activities
(Nagata, Akiko; Akagi, Yusuke; Asano, Lisa; Kotake, Kenjiro; Kawagoe, Fumihiro; Mendoza, Aileen; Masoud, Shadi Sedghi; Usuda, Kosuke; Yasui, Koji; Takemoto, Yasushi; Kittaka, Atsushi; Nagasawa, Kazuo; Uesugi, Motonari)
Tag: m, Sn, VDR, SREBP, VD

[Biochemistry 2019, 58, 5040−5051]
Role of Glycosyltransferase 25 Domain 1 in Type I Collagen Glycosylation and Molecular Phenotypes
(Terajima, Masahiko; Taga, Yuki; Sricholpech, Marnisa; Kayashima, Yukako; Sumida, Noriko; Maeda, Nobuyo; Hattori, Shunji; Yamauchi, Mitsuo)
Tag: det., Res, Lys, K, Sn, CL, COL

[Biochemistry 2019, 58, 5066−5073]
An Unusual Extender Unit Is Incorporated into the Modular Polyketide Synthase of Scopranones Biosynthesis
(Demachi, Ayumu; Uchida, Ryuji; Arima, Shiho; Nagamitsu, Tohru; Hashimoto, Junko; Komatsu, Mamoru; Kozone, Ikuko; Shin-ya, Kazuo; Tomoda, Hiroshi; Ikeda, Haruo)
Tag: BMP, CYP, OAc, A, PKS, PK, Et, O, Bu, ORF, oxidn., expt., CYP450, P450, BGC, 110-00-9

[ACS Photonics 2019, 6, 3281−3289]
Quantum Correlated Plasmons and Their Tunability in Undoped and Doped Mott-Insulator Cuprates
(Yin, Xinmao; Tang, Chi Sin; Zeng, Shengwei; Asmara, Teguh Citra; Yang, Ping; Naradipa, M. Avicenna; Trevisanutto, Paolo E.; Shirakawa, Tomonori; Kim, Beom Hyun; Yunoki, Seiji; Venkatesan, Thirumalai; Ariando, Ariando; Rusydi, Andrivo)
Tag: HL, SC, MI, Sn, SE, ipso, LE, HE, e-, CD

ナノワイヤー  
[ACS Photonics 2019, 6, 3321−3330]
Subliming GaN into Ordered Nanowire Arrays for Ultraviolet and Visible Nanophotonics
(Sergent, Sylvain; Damilano, Benjamin; Vézian, Stéphane; Chenot, Sébastien; Takiguchi, Masato; Tsuchizawa, Tai; Taniyama, Hideaki; Notomi, Masaya)
Tag: PC, sublm, Sn, UV, EB, EBL, PhC, SAS, NW, HV, UHV, QW, e-, MBE

[Chem. Sci. 2020, 11, 37−43]
A new design strategy for redox-active molecular assemblies with crystalline porous structures for lithium-ion batteries
(Nakashima, Kensuke; Shimizu, Takeshi; Kamakura, Yoshinobu; Hinokimoto, Akira; Kitagawa, Yasutaka; Yoshikawa, Hirofumi; Tanaka, Daisuke)
Tag: Li

[Chem. Sci. 2020, 11, 113−125]
Reaction mechanism, norbornene and ligand effects, and origins of meta-selectivity of Pd/norbornene-catalyzed C–H activation
(Yang, Tao; Kong, Chuncai; Yang, Shengchun; Yang, Zhimao; Yang, Sen; Ehara, Masahiro)
Tag: Nb, NBE, nbn, DFT

[Org. Biomol. Chem. 2020, 18, 47−51]
The effect of spermidine on guanine decomposition via photoinduced electron transfer in DNA
(Esumi, Mayu; Sakurai, Shunsuke; Tanaka, Makiko)
Tag: G, Gua, ET, PET, PIET, SPD, decompn., Pyr, Py, e-

ルテニウム  
[Org. Biomol. Chem. 2020, 18, 81−85]
Synthesis of lactone-fused pyrroles by ruthenium-catalyzed 1,2-carbon migration-cycloisomerization
(Watanabe, Takuma; Mutoh, Yuichiro; Saito, Shinichi)
Tag: Ru, C, PY, Ru-catalyzed

[Org. Biomol. Chem. 2020, 18, 93−101]
Design, synthesis, and evaluation of azo D–π-A dyes as photothermal agents
(Fuse, Shinichiro; Oishi, Tsukasa; Matsumura, Keisuke; Hayashi, Yoshihiro; Kawauchi, Susumu; Nakamura, Hiroyuki)
Tag: PT

[Lab Chip 2020, 20, 35−53]
Focusing of sub-micrometer particles in microfluidic devices
(Zhang, Tianlong; Hong, Zhen-Yi; Tang, Shi-Yang; Li, Weihua; Inglis, David W.; Hosokawa, Yoichiroh; Yalikun, Yaxiaer; Li, Ming)