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Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148
Graphical Abstract
Figure 1: Adamantane-based tripodal scaffolds and current work.
Scheme 1: A general strategy for the assembly of TAAD derivatives.
Scheme 2: Synthesis of acyclic precursors to 3N-TAADs, 2N,1O-TAADs, and 1N,2O-TAADs.
Scheme 3: Synthesis of 3N-TAADs, 2N,1O-TAADs, and 1N,2O-TAADs. *Yield based on compound 14.
Scheme 4: Deprotection of TAAD 8b and subsequent complexation with phenylboronic acid.
Scheme 5: Quaternization of TAADs 4c, 4e, 6a, and 8a followed by deprotection of N-Boc groups.
Figure 2: General view of the 1,4,6,10-tetraazaadamantane motif in X-ray structures of the obtained N-TAAD de...
Figure 3: (a) General structure of host–guest complexes of 3N-TAADs with water. (b) The general structure of ...
Figure 4: (a) Dynamic processes in TAADs 4 and complexation with ROH. (b) Fragment of 1H NMR spectra of Bn-4c...
Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220
Scheme 1: Precursors of nitrosoalkenes NSA.
Scheme 2: Reactions of cyclic α-chlorooximes 1 with 1,3-dicarbonyl compounds.
Scheme 3: C-C-coupling of N,N-bis(silyloxy)enamines 3 with 1,3-dicarbonyl compounds.
Scheme 4: Reaction of N,N-bis(silyloxy)enamines 3 with nitronate anions.
Scheme 5: Reaction of α-chlorooximes TBS ethers 2 with ester enolates.
Scheme 6: Assembly of bicyclooctanone 14 via an intramolecular cyclization of nitrosoalkene NSA2.
Scheme 7: A general strategy for the assembly of bicyclo[2.2.1]heptanes via an intramolecular cyclization of ...
Scheme 8: Stereochemistry of Michael addition to cyclic nitrosoalkene NSA3.
Scheme 9: Stereochemistry of Michael addition to acyclic nitrosoalkenes NSA4.
Scheme 10: Stereochemistry of Michael addition to γ-alkoxy nitrosoalkene NSA5.
Scheme 11: Oppolzer’s total synthesis of 3-methoxy-9β-estra(1,3,5(10))trien(11,17)dione (25).
Scheme 12: Oppolzer’s total synthesis of (+/−)-isocomene.
Figure 1: Alkaloids synthesized using stereoselective Michael addition to conjugated nitrosoalkenes.
Scheme 13: Weinreb’s total synthesis of alstilobanines A, E and angustilodine.
Scheme 14: Weinreb’s approach to the core structure of apparicine alkaloids.
Scheme 15: Weinreb’s synthesis of (+/−)-myrioneurinol via stereoselective conjugate addition of malonate to ni...
Scheme 16: Reactions of cyclic α-chloro oximes with Grignard reagents.
Scheme 17: Corey’s synthesis of (+/−)-perhydrohistrionicotoxin.
Scheme 18: Addition of Gilman’s reagents to α,β-epoxy oximes 53.
Scheme 19: Addition of Gilman’s reagents to α-chlorooximes.
Scheme 20: Reaction of silyl nitronate 58 with organolithium reagents via nitrosoalkene NSA12.
Scheme 21: Reaction of β-ketoxime sulfones 61 and 63 with lithium acetylides.
Scheme 22: Electrophilic addition of nitrosoalkenes NSA14 to electron-rich arenes.
Scheme 23: Addition of nitrosoalkenes NSA14 to pyrroles and indoles.
Scheme 24: Reaction of phosphinyl nitrosoalkenes NSA15 with indole.
Scheme 25: Reaction of pyrrole with α,α’-dihalooximes 70.
Scheme 26: Synthesis of indole-derived psammaplin A analogue 72.
Scheme 27: Synthesis of tryptophanes by reduction of oximinoalkylated indoles 68.
Scheme 28: Ottenheijm’s synthesis of neoechinulin B analogue 77.
Scheme 29: Synthesis of 1,2-dihydropyrrolizinones 82 via addition of pyrrole to ethyl bromopyruvate oxime.
Scheme 30: Kozikowski’s strategy to indolactam-based alkaloids via addition of indoles to ethyl bromopyruvate ...
Scheme 31: Addition of cyanide anion to nitrosoalkenes and subsequent cyclization to 5-aminoisoxazoles 86.
Scheme 32: Et3N-catalysed addition of trimethylsilyl cyanide to N,N-bis(silyloxy)enamines 3 leading to 5-amino...
Scheme 33: Addition of TMSCN to allenyl N-siloxysulfonamide 89.
Scheme 34: Reaction of nitrosoallenes NSA16 with malodinitrile and ethyl cyanoacetic ester.
Scheme 35: [4 + 1]-Annulation of nitrosoalkenes NSA with sulfonium ylides 92.
Scheme 36: Reaction of diazo compounds 96 with nitrosoalkenes NSA.
Scheme 37: Tandem Michael addition/oxidative cyclization strategy to isoxazolines 100.
Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241
Figure 1: Selected examples of polyhydrazones.
Scheme 1: Proposed approach to the synthesis of I.
Scheme 2: Synthesis of α-halogen-substituted hydrazones 1 from α-halocarbonyl compounds and acylhydrazines or...
Figure 2: Structures of polyhydrazones 3-9. Methods: A: 1 equiv of amine, 2 equiv of 1a, 2 equiv of K2CO3; B;...
Scheme 3: Synthesis of a mixed triazole-hydrazone ligand 10.
Scheme 4: Cyclisation of 11b into 1,4,6,10-tetraazaadamantane derivative.
Figure 3: General view of 13b in representation of atoms with thermal ellipsoids at 50% probability level; al...