Synthesis of P-chirogenic diphosphine oxides and their use in catalytic asymmetric Diels–Alder reaction

Matsukawa, Satoru; Sugama, Hiroshi; Imamoto, Tsuneo

doi:10.1016/s0040-4039(00)01030-3

Cited by 47 publications

(20 citation statements)

References 34 publications

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“…Here ee = enantiomeric excess. Khiar (23) in 1993 and Imamoto and coworkers (24) in 2000 devised other bidentate ligands, such as C 2 symmetric bis (sulfoxides) and diphosphine oxides, respectively, for an asymmetric Diels-Alder reaction that resulted in lower diastereo-and enantioselectivity for the reaction (Scheme 13).…”

Section: The [4 + 2] Cycloadditionmentioning

confidence: 99%

“…Especially when the reactive intermediates are toxic and explosive. Considering these facts, Morandi and Carreira recently developed (43) a new procedure for cyclopropanation that minimized the risk as well as the time and (24) when the ejected diazomethane was transferred to the organic layer. Except for being hydrophilic, both the electron-rich and the electron-poor subtrates were well tolerated under optimal reaction condition (Table III).…”

Section: B Cyclopropanationmentioning

confidence: 99%

“…Except for being hydrophilic, both the electron-rich and the electron-poor subtrates were well tolerated under optimal reaction condition (Table III). Carreira and co-workers (44) developed a cyclopropanation reaction (Scheme 27, dr = diastereomeric ratio) using the same catalyst Fe(TPP)Cl (24) and glycine ethyl ester hydrochloride as the inexpensive and safe carbene source to yield the trans-cyclopropyl ester selectively. Trifluoromethylated cyclopropanes are important compounds in drug delivery (45), though very few synthetic methods were reported for their preparation.…”

Section: B Cyclopropanationmentioning

confidence: 99%

“…Carreira and co-workers (46,47) recently reported potentially applicable methods for the synthesis of trifluoromethylated cyclopropanes by using trifluoroethylamine hydrochloride as the carbene source. Tandem cyclopropanation occurred in the presence of 3 mol% Fe(TPP)Cl (24) and saturated NaNO 2 solution to generate carbene. Both electron-rich and electron-deficient dienes were good substrates (Table IV) for this transformation, but it was unable to cyclopropanate 1,2-transsubstituted double bonds.…”

Section: B Cyclopropanationmentioning

confidence: 99%

See 3 more Smart Citations

Iron Catalysis in Synthetic Chemistry

Rana

Modak

Maity

et al. 2014

Progress in Inorganic Chemistry: Volume 59

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Section: The [4 + 2] Cycloadditionmentioning

confidence: 99%

Section: B Cyclopropanationmentioning

confidence: 99%

Section: B Cyclopropanationmentioning

confidence: 99%

Section: B Cyclopropanationmentioning

confidence: 99%

See 2 more Smart Citations

Iron Catalysis in Synthetic Chemistry

Rana

Modak

Maity

et al. 2014

Progress in Inorganic Chemistry: Volume 59

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“…Other bidentate ligands such as phosphorus dioxide ligand 54 [88] and disulfoxide ligand 55 [89] were also developed but with lower efficiency.…”

Section: Scheme 42mentioning

confidence: 99%

Recent advances in the iron-catalyzed cycloaddition reactions

Wang

Wan

2012

Chin. Sci. Bull.

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The rapid generation of molecular in a relatively easy manner has made the cycloaddition reaction a powerful tool in the synthesis of different membered ring compounds. Clearly, iron catalysts are becoming a much more interesting and viable choice for this purpose. In this review, a number of promising results in the iron catalyzed cycloaddition reactions in the last decades were summarized. Special attention has been paid to the asymmetric cycloaddition reactions. cycloaddition, iron catalyst, asymmetric Citation:Wang C X, Wan B S. Recent advances in the iron-catalyzed cycloaddition reactions. Chin Sci Bull, 2012, 57: 23382351, doi: 10.1007/s11434-012-5141-z Cycloaddition reaction, which can construct several bonds simultaneously in a single step, is one of the most powerful strategies for the synthesis of cyclic compounds from various unsaturated substrates such as alkynes, alkenes, allenes, nitriles, aldehydes, ketones, imines, etc. Three-, four-, five-, six-or seven-membered rings are obtained through these transformations. The high atom-efficiency, as well as the good tolerance of different functional groups, continues to draw many chemists' attention to this field. In particular, great efforts have been devoted to the development of novel and efficient catalytic systems. However, harsh reaction conditions are often required including heat, light, high pressure or sonication, and the lack of chemo-and/or regioselectivity is also an important problem. Over the past decades, the use of transition metal catalysts has contributed significantly to the development of the cycloaddition reactions and good selectivities were obtained [1]. Among all the available transition metals, iron is generally regarded as one of the most inexpensive, abundant, benign and relatively non-toxic metals [2]. Many transformations have been effectively promoted by iron catalysts, and excellent reviews on the iron-catalyzed reactions are available [3][4][5][6][7][8][9][10][11][12][13][14][15]. Bolm and co-workers [3] summarized the most important transformations with the aid of iron catalysts in 2004, including addition, substitution, cycloaddition, reduction and other reactions. At a later time, they also reviewed the oxidative C-C coupling reactions [4] and the development of carbon-heteroatom and heteroatom-heteroatom bond formation under iron catalysts [5]. The uses of FeCl 3 as catalyst in organic synthesis were covered by Padrón [6] and Bolm [4], and the cross coupling reactions were discussed in detail by Fürstner [7,8]. Recently, direct C-H transformation via iron catalysis was summarized by Shi and co-workers [9]. Applications of iron catalysts on other reactions were also summarized by Bauer [10] However, despite the aforementioned contributions, reviews mainly focus on the iron-catalyzed cycloaddition reactions are rather rare [15]. In this review, we will point out recent advances in this field, most contributions going from 2004 to Nov. 2011. Although every effort has been made to avoid repetition, some overlap with the ...

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Organic Transformations Promoted by Lewis Acid Iron Catalysts

Vrancken¹,

Campagne²

2013

Patai's Chemistry of Functional Groups

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Iron salts of high oxidation states, Fe(II) and Fe(III), possess strong Lewis acid properties and are able to activate a wide range of functionalities. These properties, associated with low toxicity, abundance, low price together with more practical aspects, are witnessed by the blossoming of this field in the last few years. Beyond traditional activation of CX and CX bonds, more recent applications involving the generation of iron enolates and oxocarbeniums species, and the activation of CC and CC bonds are surveyed. A special emphasis is given to successive electrophilic and/or nucleophilic activations of different functionalities, which allow domino and one‐pot processes.

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Synthesis of P-chirogenic diphosphine oxides and their use in catalytic asymmetric Diels–Alder reaction

Cited by 47 publications

References 34 publications

Iron Catalysis in Synthetic Chemistry

Iron Catalysis in Synthetic Chemistry

Recent advances in the iron-catalyzed cycloaddition reactions

Organic Transformations Promoted by Lewis Acid Iron Catalysts

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