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3 article(s) from Ioffe, Sema L

Diels–Alder reaction of β-fluoro-β-nitrostyrenes with cyclic dienes

Savva A. Ponomarev,
Roman V. Larkovich,
Alexander S. Aldoshin,
Andrey A. Tabolin,
Sema L. Ioffe,
Jonathan Groß,
Till Opatz and
Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2021, 17, 283–292, doi:10.3762/bjoc.17.27

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Graphical Abstract

Scheme 1: Scope of the nitrostyrenes 1 in the Diels–Alder reaction with CPD (dr = exo:endo).

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Figure 1: The structure assignment of norbornenes 2 by ¹H (a) and NOE (b) NMR spectroscopy.

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Figure 2: ¹³C NMR spectrum of the mixture of exo- and endo-isomers of norbornene 2l.

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Figure 3: The predicted reaction pathway for the Diels–Alder reaction of nitrostyrene 1h with CPD is displaye...

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Scheme 2: The Diels–Alder reaction of nitrostyrene 1h with spiro[2.4]hepta-4,6-diene.

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Scheme 3: Diels–Alder reaction of nitrostyrenes 1 with CHD (dr = exo:endo). (а) Reaction under microwave acti...

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Scheme 4: Kinetic study of reactions of 1h with CPD and CHD.

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Figure 4: Kinetic curves for the reactions of nitrostyrene 1h with CPD (50–130 °C) and CHD at 110 °C.

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Scheme 5: The Diels–Alder reaction of the nitrostyrene 1h with 1-methoxy-1,3-cyclohexadiene.

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Scheme 6: Selected chemical transformations of norbornenes 2 (dr = exo:endo).

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Published 27 Jan 2021

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Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective

Yaroslav D. Boyko,
Valentin S. Dorokhov,
Alexey Yu. Sukhorukov and
Sema L. Ioffe

Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220

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Scheme 1: Precursors of nitrosoalkenes NSA.

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Scheme 2: Reactions of cyclic α-chlorooximes 1 with 1,3-dicarbonyl compounds.

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Scheme 3: C-C-coupling of N,N-bis(silyloxy)enamines 3 with 1,3-dicarbonyl compounds.

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Scheme 4: Reaction of N,N-bis(silyloxy)enamines 3 with nitronate anions.

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Scheme 5: Reaction of α-chlorooximes TBS ethers 2 with ester enolates.

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Scheme 6: Assembly of bicyclooctanone 14 via an intramolecular cyclization of nitrosoalkene NSA2.

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Scheme 7: A general strategy for the assembly of bicyclo[2.2.1]heptanes via an intramolecular cyclization of ...

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Scheme 8: Stereochemistry of Michael addition to cyclic nitrosoalkene NSA3.

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Scheme 9: Stereochemistry of Michael addition to acyclic nitrosoalkenes NSA4.

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Scheme 10: Stereochemistry of Michael addition to γ-alkoxy nitrosoalkene NSA5.

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Scheme 11: Oppolzer’s total synthesis of 3-methoxy-9β-estra(1,3,5(10))trien(11,17)dione (25).

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Scheme 12: Oppolzer’s total synthesis of (+/−)-isocomene.

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Figure 1: Alkaloids synthesized using stereoselective Michael addition to conjugated nitrosoalkenes.

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Scheme 13: Weinreb’s total synthesis of alstilobanines A, E and angustilodine.

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Scheme 14: Weinreb’s approach to the core structure of apparicine alkaloids.

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Scheme 15: Weinreb’s synthesis of (+/−)-myrioneurinol via stereoselective conjugate addition of malonate to ni...

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Scheme 16: Reactions of cyclic α-chloro oximes with Grignard reagents.

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Scheme 17: Corey’s synthesis of (+/−)-perhydrohistrionicotoxin.

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Scheme 18: Addition of Gilman’s reagents to α,β-epoxy oximes 53.

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Scheme 19: Addition of Gilman’s reagents to α-chlorooximes.

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Scheme 20: Reaction of silyl nitronate 58 with organolithium reagents via nitrosoalkene NSA12.

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Scheme 21: Reaction of β-ketoxime sulfones 61 and 63 with lithium acetylides.

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Scheme 22: Electrophilic addition of nitrosoalkenes NSA14 to electron-rich arenes.

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Scheme 23: Addition of nitrosoalkenes NSA14 to pyrroles and indoles.

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Scheme 24: Reaction of phosphinyl nitrosoalkenes NSA15 with indole.

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Scheme 25: Reaction of pyrrole with α,α’-dihalooximes 70.

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Scheme 26: Synthesis of indole-derived psammaplin A analogue 72.

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Scheme 27: Synthesis of tryptophanes by reduction of oximinoalkylated indoles 68.

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Scheme 28: Ottenheijm’s synthesis of neoechinulin B analogue 77.

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Scheme 29: Synthesis of 1,2-dihydropyrrolizinones 82 via addition of pyrrole to ethyl bromopyruvate oxime.

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Scheme 30: Kozikowski’s strategy to indolactam-based alkaloids via addition of indoles to ethyl bromopyruvate ...

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Scheme 31: Addition of cyanide anion to nitrosoalkenes and subsequent cyclization to 5-aminoisoxazoles 86.

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Scheme 32: Et₃N-catalysed addition of trimethylsilyl cyanide to N,N-bis(silyloxy)enamines 3 leading to 5-amino...

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Scheme 33: Addition of TMSCN to allenyl N-siloxysulfonamide 89.

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Scheme 34: Reaction of nitrosoallenes NSA16 with malodinitrile and ethyl cyanoacetic ester.

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Scheme 35: [4 + 1]-Annulation of nitrosoalkenes NSA with sulfonium ylides 92.

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Scheme 36: Reaction of diazo compounds 96 with nitrosoalkenes NSA.

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Scheme 37: Tandem Michael addition/oxidative cyclization strategy to isoxazolines 100.

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Review

Published 23 Oct 2017

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Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

Artem N. Semakin,
Aleksandr O. Kokuev,
Yulia V. Nelyubina,
Alexey Yu. Sukhorukov,
Petr A. Zhmurov,
Sema L. Ioffe and
Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

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Figure 1: Selected examples of polyhydrazones.

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Scheme 1: Proposed approach to the synthesis of I.

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Scheme 2: Synthesis of α-halogen-substituted hydrazones 1 from α-halocarbonyl compounds and acylhydrazines or...

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Figure 2: Structures of polyhydrazones 3-9. Methods: A: 1 equiv of amine, 2 equiv of 1a, 2 equiv of K₂CO₃; B;...

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Scheme 3: Synthesis of a mixed triazole-hydrazone ligand 10.

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Scheme 4: Cyclisation of 11b into 1,4,6,10-tetraazaadamantane derivative.

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Figure 3: General view of 13b in representation of atoms with thermal ellipsoids at 50% probability level; al...

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Published 21 Nov 2016

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