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Search for "phosphaferrocene" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

Almaz A. Zagidullin,
Farida F. Akhmatkhanova,
Mikhail N. Khrizanforov,
Robert R. Fayzullin,
Tatiana P. Gerasimova,
Ilya A. Bezkishko and
Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

; electrochemical properties; phosphacyclopentadienide anion; phosphaferrocene; phosphonium salt; phosphorus heterocycle; Introduction Among the various heterometallocenes reported to date, phosphaferrocenes are by far the most investigated because of their structural and electronic features [1][2] and remain the

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Scheme 1: Synthesis of bis(chlorophenyl)acetylenes 3.

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Scheme 2: Synthesis of 1,2,3-tris(chlorophenyl)cyclopropenylium bromides 5 and tributyl(1,2,3-tris(chlorophen...

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Figure 1: ORTEP representations for cations 5c (a) and 6c (b) at the 50% probability level. Bromide anion and...

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Scheme 3: Synthesis of 3,4,5-tris(chlorophenyl)-1,2-diphosphacyclopentadienides 7 and 3,4,5-tris(chlorophenyl...

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Figure 2: Considered conformations of 8b-I and 8b-II.

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Figure 3: Top: experimental UV–vis spectra of 8с (black) and 8b (red). Bottom: broadened calculated UV–vis sp...

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Figure 4: Frontier orbitals of 8b-II contributing to absorption bands at about 380 nm.

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Figure 5: Cyclic voltammograms of 3,4,5-triaryl-1,2-diphosphaferrocenes 8b and 8c in CH₃CN on glassy carbon e...

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Full Research Paper

Published 27 Sep 2022

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Organocatalyzed enantioselective desymmetrization of aziridines and epoxides

Ping-An Wang

Beilstein J. Org. Chem. 2013, 9, 1677–1695, doi:10.3762/bjoc.9.192

asymmetric ring-opening of epoxides remained stagnant for sixteen years. In 1997, Fu [79] and colleagues have developed a phosphaferrocene OC-56 for the organocatalytic ring-opening of epoxides with trimethylsilyl chloride (TMSCl) to provide trans O-TMS protected vicinal chlorohydrins in quantitative yields

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Figure 1: The catalyzed enantioselective desymmetrization.

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Figure 2: Cinchona alkaloid-derived catalysts OC-1 to OC-11.

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Scheme 1: The enantioselective desymmetrization of meso-aziridines in the presence of selected Cinchona alkal...

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Figure 3: Cinchona alkaloid-derived catalysts OC-12 to OC-19.

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Scheme 2: The enantioselective ring-opening of aziridines in the presence of OC-16.

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Scheme 3: OC-16 catalyzed enantioselective ring-opening of aziridines.

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Figure 4: The chiral phosphoric acids catalysts OC-20 and OC-21.

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Scheme 4: OC-20 and OC-21 catalyzed enantioselective desymmetrization of meso-aziridines.

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Figure 5: The proposed mechanism for chiral phosphorous acid-induced enantioselctive desymmetrization of meso...

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Scheme 5: OC-21 catalyzed enantioselective desymmetrization of meso-aziridines by Me₃SiSPh.

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Scheme 6: OC-21 catalyzed the enantioselective desymmetrization of meso-aziridines by Me₃SiSePh/PhSeH.

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Figure 6: L-Proline and its derivatives OC-22 to OC-27.

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Scheme 7: OC-23 catalyzed enantioselective desymmetrization of meso-aziridines.

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Figure 7: Proposed bifunctional mode of action of OC-23.

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Figure 8: The chiral thioureas OC-28 to OC-44 for the desymmetrization of meso-aziridines.

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Scheme 8: Desymmetrization of meso-aziridines with OC-41.

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Figure 9: The chiral guanidines (OC-45 to OC-48).

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Scheme 9: OC-46 catalyzed desymmetrization of meso-aziridines by arylthiols.

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Scheme 10: Desymmetrization of cis-aziridine-2,3-dicarboxylate.

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Figure 10: The proposed activation mode of OC-46.

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Scheme 11: The enantioselective desymmetrization of meso-aziridines by amine/CS₂ in the presence of OC-46.

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Figure 11: The chiral 1,2,3-triazolium chlorides OC-49 to OC-55.

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Scheme 12: The enantioselective desymmetrization of meso-aziridines by Me₃SiX (X = Cl or Br) in the presence o...

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Figure 12: Early organocatalysts for enantioselective desymmetrization of meso-epoxides.

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Scheme 13: Attempts of enantioselective desymmetrization of meso-epoxides in the presence of OC-58 or OC-60.

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Scheme 14: The enantioselective desymmetrization of a meso-epoxide containing one P atom.

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Figure 13: Some chiral phosphoramide and chiral phosphine oxides.

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Scheme 15: OC-62 catalyzed enantioselective desymmetrization of meso-epoxides by SiCl₄.

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Figure 14: The proposed mechanism of the chiral HMPA-catalyzed desymmetrization of meso-epoxides.

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Scheme 16: The enantioselective desymmetrization of meso-epoxides in the presence of OC-63.

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Figure 15: The Chiral phosphine oxides (OC-70 to OC-77) based on an allene backbone.

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Scheme 17: OC-73 catalyzed enantioselective desymmetrization of meso-epoxides by SiCl₄.

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Figure 16: Chiral pyridine N-oxides used in enantioselective desymmetrization of meso-epoxides.

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Scheme 18: Catalyzed enantioselective desymmetrization of meso-epoxides in the presence of OC-80 or OC-82.

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Figure 17: Chiral pyridine N-oxides OC-85 to OC-94.

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Scheme 19: Enantioselective desymmetrization of cis-stilbene oxide by using OC-85 to OC-92 as catalysts.

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Figure 18: A novel family of helical chiral pyridine N-oxides OC-95 to OC-97.

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Scheme 20: Desymmetrization of meso-epoxides catalyzed by OC-95 to OC-97.

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Scheme 21: OC-98 catalyzed enantioselective desymmetrization of meso-epoxides by SiCl₄.

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Published 15 Aug 2013

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