出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.2, no.5, pp.418-422,382, 1944-05-01 (Released:2010-10-20)

著者

小林 正治 原 倫太朗 佐藤 一樹 和田 猛 吉川 真人 味上 達

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.79, no.6, pp.595, 2021-06-01 (Released:2021-06-09)

著者

安藤 香織

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.59, no.5, pp.418-419, 2001-05-01 (Released:2009-11-13)

参考文献数

5

被引用文献数

1 1

著者

菅原 正

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.47, no.4, pp.306-320, 1989-04-01 (Released:2010-01-22)

参考文献数

53

被引用文献数

8 8

---

Design of high spin organic molecules is described in three categories ; use of strong exchange interaction in one-center diradicals, non-Kekule molecules, anti-aromatic annulenes including charged species. Magnetic behavior of metapoly-phenylmethylene (8) is discussed as a model of one-dimentional organic ferromagnet. Intermolecular interaction among triplet diphenyl carbenes generated in host crystals of a diazo precursor is interpreted in terms of the results in a model system of [2, 2] paracyclophanedicarbenes.An attempt to realize ferromagnetic material utilizing CT interaction is rewared with a success in the case of decamethylferrocene-TCNE complex. Finally the electronic requirement for realizing organic ferromagnet is discussed in reference to that for organic conductors.

著者

古谷 正之

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.22, no.11, pp.899-916, 1964-11-01 (Released:2010-06-28)

著者

淺原 光太郎 柏原 美勇斗 武藤 慶 中尾 佳亮 山口 潤一郎

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.79, no.1, pp.11-21, 2021-01-01 (Released:2021-01-09)

参考文献数

108

被引用文献数

1

---

Transition metal-catalyzed cross-coupling between aryl halides and nucleophiles is one of the most reliable C-C and C-heteroatom bond forming reactions. However, preparation of haloarenes usually requires multi-step operation, making the whole cross-coupling process inefficient. Nitroarenes, synthesized by a single-step nitration of arenes, can be attractive alternatives as electrophiles in cross-coupling methodology, but inherent inertness of C(sp2)-NO2 bonds toward metal catalysts has been a bottleneck of general denitrative transformations. Recently, we have overcome this obstacle and achieved direct activation of Ar-NO2 bonds by using Pd/BrettPhos catalysis. Herein, we describe the development of denitrative couplings by Pd/BrettPhos catalyst and its unique suitability from a mechanistic point of view. Deep understanding of reaction mechanism also enabled us to design more active Pd/NHC system.

著者

王子田 彰夫 宮原 芳文 浜地 格

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.64, no.2, pp.141-150, 2006-02-01 (Released:2010-10-20)

参考文献数

36

被引用文献数

1 1

---

In recent years, a variety of chemical methods for selective labeling or functional modulation of protein of interest has been developed. In this article, we focus on synthetic organic chemistry for protein modification, especially on the recent developments of the bioorthogonal reactions, which enable to hybridize an artificial small molecule to a protein of interest with a site-selective manner. On the other hand, covalent bond formation of protein with a small molecule has also been recognized as a powerful strategy to regulate protein functions, and enormous efforts have been devoted to develop selective irreversible inhibitors for proteins, especially for the families of proteases, in the research field of medicinal chemistry. We also provide an overview of the irreversible inhibitors, including their recent advancements and some applications for proteome analysis or drug discovery. In addition, we report herein our original method (P-PALM) for site-selective modification of a protein using the photo-affinity labeling technique. The utility of the P-PALM method has been successfully demonstrated in the modifications of the lectin into the new fluorescent saccharide biosensors.

著者

服部 倫弘 村松 渉 山本 尚

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.79, no.5, pp.382-390, 2021-05-01 (Released:2021-05-11)

参考文献数

78

被引用文献数

3

---

Peptides, which are elongated of peptides chain of amino acids linked by amide bonds, are elementary components in living systems and regulate many biological processes. Since the solid-phase peptide synthesis was introduced by Merrifield in 1964, chemical synthesis of peptides using solid-phase system has emerged as a valuable method due to its ease of operation and rapid synthesis of desired peptides. However, despite of the effectiveness of the solid-phase approach, typical reaction requires excess amounts of coupling reagents, bases, and amino acids to achieve maximum conversion. And the ease of operation led to accumulate undesired segments together with target peptide because solid-phase system is generally carried out by coupling amino acids with N-terminal amino acid residue of peptides in a stepwise approach without any isolation and characterization at each step. To solve these issues, we focused on the development of catalytic liquid-phase synthesis, which has advantage of isolating the growing peptide chain from reaction solution after each coupling step. Although several liquid-phase methods have been developed, there is a still considerable room for the improvement of racemization, generality, and ligation reaction. In this view, we have developed a mild, practical, and efficient methods based on substrate-control by using boronic acid, niobium, and tantalum as catalysts. Our methods can be applied for a broad variety of amino acids to furnish the desired peptides in excellent yields without significant loss of stereochemical integrity. The developed straightforward approach overcome a lot of problem associated with peptide synthesis. This article describes our recent achievement based on catalytic substrate-controlled peptide synthesis.

著者

大野 祥平 有澤 光弘

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.79, no.1, pp.22-33, 2021-01-01 (Released:2021-01-09)

参考文献数

50

---

Cyclization reactions between two multiple bonds have been fascinating processes that allow the discovery of new reactions and the construction of carbo- and/or heterocycles. Among multiple bonds, heteroatom-substituted olefins have different reactivity from those having heteroatom on the allylic or homoallylic position, but the reactions have been reported few cases until the 2000s. Lately, the reactions between multiple bonds and heteroatom-substituted olefins have been reported, and this review explains them by the reaction class.

著者

高田 正郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.51, no.5, pp.440-441, 1993-05-01 (Released:2009-11-16)

参考文献数

9

著者

田中 津久志 矢崎 亮 大嶋 孝志

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.79, no.5, pp.417-426, 2021-05-01 (Released:2021-05-11)

参考文献数

72

---

Enolization of carboxylic acid derivatives is the central science of fundamental carbonyl chemistry. The catalytic methods to activate carboxylic acid remained unexplored due to the intrinsic low acidity of α-protons, although enormous examples of catalytic activation (enolization) method for aldehydes, ketones, and ester derivatives have been reported. The innate Brønsted acidic carboxylic acid functionality also disrupts the deprotonation of α-protons. Therefore, more than two equivalents of a strong base such as lithium diisopropylamide are required for efficient enolization, which makes chemoselective enolization of carboxylic acid over more acidic carbonyls a formidable task. Furthermore, recent enolization methods were only applied to redox-neutral coupling using 2e- electrophiles and catalytic α-functionalization of carboxylic acids through a 1e- radical process, which could complement the chemoselectivity, and functional group tolerance restricted in the classical 2e- ion reaction, has never been achieved. Herein, we developed chemoselective catalytic activation of carboxylic acid equivalent, acylpyra-zole, and carboxylic acid for a 1e- radical process without external addition of stoichiometric amounts of Brønsted base. The present chemoselective catalysis could be applied to late-stage α-amination and oxidation, allowing for concise access to highly versatile unnatural α-amino acid and hydroxy acid derivatives. Moreover, chemoselective α-functionalization of less reactive carboxylic acids was achieved over innately more reactive carbonyl functionalities.

著者

河内 卓彌 百足 勉 Jonathan A. Ellman

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.62, no.2, pp.128-139, 2004-02-01 (Released:2009-11-13)

参考文献数

43

被引用文献数

7 10

---

tert-Butanesulfinyl imines are exceedingly versatile intermediates for the asymmetric synthesis of amines. Aldimines 15 and ketimines 16 are prepared in high yields under mild conditions by condensing enantiomerically pure tert-butanesulfinamide 10, either enantiomer of which is readily synthesized in large scale from inexpensive reagents, with a wide range of aldehydes and ketones. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition function as a versatile protecting group of the amines, which is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched amines, α, α-dibranched amines, α- and β-amino acids, 1, 2- and 1, 3-amino alcohols, and α-trifluoromethylamines are efficiently synthesized using this methodology.

著者

山根 靖弘 坂井 和男

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.39, no.11, pp.1105-1113, 1981-11-01 (Released:2009-11-13)

参考文献数

63

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最近, 生体微量金属に関する研究に一層の関心が集まってきており, 金属欠乏症, 遺伝性疾病やがんなどにおける金属代謝の異常など, 金属と疾病との関連が一段と注目されている.また, 生活環境中の重金属濃度の増加とともに, 環境汚染と関連した有害性金属による疾病の発生に対しても関心が高まっている.そこで金属と疾病との関連にっいて, 最近の研究を中心に述べる.

著者

小方 芳郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.33, no.11, pp.821-833, 1975-11-01 (Released:2009-11-13)

参考文献数

90

著者

森 聖治 中村 栄一

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.61, no.2, pp.144-151, 2003-02-01 (Released:2009-11-13)

参考文献数

41

被引用文献数

1 3

---

Recent development in the use of high-precision quantum chemical calculations for the investigation of the mechanisms of synthetically important organometallic reaction is reviewed. The review is focused on the following issues that have be the subject of much discussion in the society of synthetic organic chemists for many years : (1) Nucleophilic addition to carbonyl compounds, (2) osmium-tetraoxide-catalyzed dihydroxylation, (3) organocopper reactions, and (4) Simmons-Smith cyclopropanation.

著者

春沢 信哉 栗原 拓史

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.53, no.8, pp.712-723, 1995-08-01 (Released:2009-11-16)

参考文献数

36

被引用文献数

4 5

---

A highly stereoselective synthesis of (Z) - or (E) -double bonds in 10-membered thiolcarbonates is achieved by the [3, 3] sigmatropic rearrangement of 8-membered thionocarbonates which proceeds through the chairlike vs. boatlike transition states. The formation of the 8-membered intermediates followed by their [3, 3] sigmatropic rearrangements were investigated by experiments and theoretical calculations. Their utilities of this methodology have been demonstrated by the unique and stereoselective synthesis of (-)-yellow scale pheromone. Moreover, medium-membered heterocyclic allenes were synthesized by this method. The structure and reactivity of a new type of strained 8-membered allene were also examined. Using this method combined with a novel application of the newly developed SmI2-HMPA reduction of the cyclic allene, the antifungal constituent of a Sapium japonicum was synthesized.

著者

徳山 英利 中村 正治

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.63, no.5, pp.523-538, 2005-05-01 (Released:2009-11-13)

参考文献数

102

被引用文献数

16 20

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Among non-conventional stimulations to accelerate organic reactions, high-pressure, ultrasound irradiation, and microwave irradiation are representative methods and are now becoming more and more popular in laboratories. This review focuses on organic reactions under microwave irradiation since this technique has attracted broad range of interest from the scientific and practical viewpoints. After the brief description on the historical and theoretical backgrounds of the dielectric heating, microwave effects, practical aspects of microwave heating (choice of solvent and microwave reactors), scope, and limitations of microwave-assisted synthetic reactions are discussed.

著者

Kei Gotot Takayuki Kawashima

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.63, no.11, pp.1157-1170, 2005-11-01 (Released:2009-11-13)

参考文献数

52

被引用文献数

6 6

---

Several kinds of bowl-type molecules were designed for regulation of the reactivities of the functional groups in their cavities, especially for kinetic stabilization of highly reactive species which have been difficult of access by conventional methods. The “peripheral steric protection” by these molecular cavities effectively prevents the bimolecular decomposition of the reactive species such as dimerization or self-condensation, and enabled the isolation of various species including a sulfenic acid, a selenenic acid, an S-nitrosothiol, and a Se-nitrososelenol, which have been known as important but elusive intermediates in biological reactions. Utilization of the molecular bowls as the ligands for transition metal complexes is also described.

著者

赤井 周司

出版者

公益社団法人 有機合成化学協会

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.79, no.2, pp.99, 2021-02-01 (Released:2021-02-10)

著者

平林 一徳 森 敦紀

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.58, no.10, pp.926-933, 2000 (Released:2009-11-13)

参考文献数

35

被引用文献数

4 5

---

This article reviews organic chemistry of siloxane and silanol involving the preparative method as well as applications towards organic synthesis. Chapter 1 deals with the formation of siloxane bond and reactions of thus prepared siloxane compounds. Chapter 2 covers recent preparative methods for silanols and new synthetic reaction using silanol involving 1) utilization of silanol oxygen that serves as a base or a nucleophile, 2) transformation of neighboring functionality on the silicon substituent based on the interaction of silanol oxygen with an organometallic reagent, and 3) transformation of a carbon silicon bond of silanols directed to novel carbon-carbon bond forming reactions.