1,2,3,4,5,6-Hexahydrophosphinine 1-oxides with an exocyclic P-function at position 3: diastereoselective synthesis, stereostructure and conformation

Keglevich, György; Sipos, Melinda; Körtvélyesi, Tamás; Imre, Tı́mea; Tőke, Lásʐló

doi:10.1016/j.tetlet.2005.01.073

Cited by 17 publications

(20 citation statements)

References 4 publications

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“…The relative position of the two P(III)-functions was confirmed by 31 P NMR spectral data and quantum chemical calculations [65,[84][85][86][87][88]. It is noteworthy, that the platinum complex of the 3-diphenylphosphino-1-phenyl-1,2,3,6-tetrahidrophosphinine (36*) was also prepared in an optically active form [65].…”

Section: Complexation Reactions Of Cyclic Phosphines and Bisphosphinesmentioning

confidence: 78%

Environmentally Friendly Chemistry with Organophosphorus Syntheses in Focus

Keglevich

Grűn²,

Bagi³

et al. 2015

Period. Polytech. Chem. Eng.

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The use of the microwave (MW) Keywords organophosphorus chemistry, green chemistry, microwave, resolution, platinum complexes, dronic acids/dronates IntroductionIn this minireview, our recent results in environmentallyfriendly ("green") chemistry have been summarized. In the first sub-chapter the usefulness of the microwave technique is shown in organophosphorus chemistry. The second sub-chapter summarizes our results on the resolution of cyclic phosphine oxides, as precursors for P-ligands and on the synthesis of platinum complexes as potential catalysts. Catalysts are of utmost importance from the point of view of green chemistry. The last sub-chapter comprises our experiences on the optimization of the synthesis of dronic acid derivatives that are important drugs against bone diseases.

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Section: Complexation Reactions Of Cyclic Phosphines and Bisphosphinesmentioning

confidence: 78%

Environmentally Friendly Chemistry with Organophosphorus Syntheses in Focus

Keglevich

Grűn²,

Bagi³

et al. 2015

Period. Polytech. Chem. Eng.

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“…Catalytic hydrogenation of 1-phenyl-3-diphenylphosphinoxido-and 3-dialkylphosphono-1,2,3,6-tetrahydrophosphinine oxides 1a-c gave the corresponding 1,2,3,4,5,6-hexahydrophosphinine oxides 2a-c as single diastereomers (Scheme 1) [9].…”

Section: Resultsmentioning

confidence: 99%

“…Hydrogenation of the 1-ethoxy-3-dialkylphosphono starting materials (3a,b) led to the products (4a,b) as a mixture of a major (4-1) and a minor (4-2) diastereomer (Scheme 2) [9]. Stereostructures of the products (2 and 4) were identified by SCHEME 1 stereospecific 3 J (P,C) and 3 J (P,H) NMR couplings [9].…”

Section: Resultsmentioning

confidence: 99%

“…Stereostructures of the products (2 and 4) were identified by SCHEME 1 stereospecific 3 J (P,C) and 3 J (P,H) NMR couplings [9].…”

Section: Resultsmentioning

confidence: 99%

“…Simple 1,2,3,4,5,6-hexahydrophosphinine oxides were synthesized by the catalytic hydrogenation of 1,2-dihydrophosphinine oxides [4], or even by the reduction of 3-phosphabicyclo[3.1.0]hexane 3-oxides [5,6]. Recently, 1,2,3,6-tetrahydrophosphinine oxides with an exocyclic P-moiety in position 3 were introduced [7,8] that were suitable starting materials for the title compounds [9]. In this paper, the results of a quantum chemical study on the possible conformations of 3-P(O)Y 2 substituted 1,2,3,4,5,6-hexahydrophosphinine oxides are summarized.…”

Section: Introductionmentioning

confidence: 99%

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A theoretical study on the conformation of 3-phosphinoxido- and 3-phosphono-1,2,3,4,5,6-hexahydrophosphinine 1-oxides

2005

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New P‐ligands: 3‐(ethyl‐phenylphosphinato‐) 1,2,3,6‐tetrahydro‐ and 1,2,3,4,5,6‐hexahydrophosphinine derivatives

Sipos

Körtvélyesi

Ujj

et al. 2007

Heteroatom Chemistry

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The trimethylaluminum-mediated Michael addition of ethyl phenyl-H-phosphinate to 1,2-dihydrophosphinine oxides (1A) yielded 3-(EtOPhP(O))-1,2,3,6-tetrahydrophosphinine oxides (4) in a selective manner, as a mixture of only two diastereomers. In the above type of reactions (e.g., in that of 1Aa and Ph 2 P(O)H), Me 3 Al could not be substituted by microwave irradiation due to low efficiency. Catalytic hydrogenation of the Michael adducts (4) led to 3-(EtOPhP(O)-1,2,3,4,5,6-hexahydrophosphinine oxides 5, in the case of P-phenyl substituent (5a), as a mixture of only two diastereomers, while in the instance of the P-ethoxy derivative (5b), as a mixture of four isomers. Stereostructure of the products (5) was substantiated on the basis of analogies and stereospecific NMR couplings. The predominant conformations of compounds 4a, 4b, 5a, and 5b-1 were determined by HF/6-31G * calculations. Reduction of P(1)-Ph heterocycles 4a and 5a by phenylsilane resulted in monodeoxygenation to afford P-ligands 6 and 8, respectively, that were protected as the corresponding phosphine boranes (7 and 9, respectively). C 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:747-753, 2007; Published online in Wiley InterScience (www.interscience.wiley.com).

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1,2,3,4,5,6-Hexahydrophosphinine 1-oxides with an exocyclic P-function at position 3: diastereoselective synthesis, stereostructure and conformation

Cited by 17 publications

References 4 publications

Environmentally Friendly Chemistry with Organophosphorus Syntheses in Focus

Environmentally Friendly Chemistry with Organophosphorus Syntheses in Focus

A theoretical study on the conformation of 3-phosphinoxido- and 3-phosphono-1,2,3,4,5,6-hexahydrophosphinine 1-oxides

New P‐ligands: 3‐(ethyl‐phenylphosphinato‐) 1,2,3,6‐tetrahydro‐ and 1,2,3,4,5,6‐hexahydrophosphinine derivatives

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