Aza‐Henry Reaction of Isatin Ketimines with Methyl 4‐Nitrobutyrate en Route to Spiro[piperidine‐3,3′‐oxindoles]

Holmquist, Melireth; Blay, Gonzalo; Muñoz, M. Carmen; Pedro, José R.

doi:10.1002/adsc.201500716

Cited by 26 publications

(5 citation statements)

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“…The metal-free generation of oxime species from nitro compounds is typically based on their reduction with Sn II or active hydrogen (for recent works, see refs and and ref , respectively). These agents reduce R 1 R 2 CHNO 2 and provide expedient access to nonfunctionalized oximes R 1 R 2 CNOH.…”

Section: Metal-mediated Generation Of Oximesmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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This review classifies and summarizes the past 10-15 years of advancements in the field of metal-involving (i.e., metal-mediated and metal-catalyzed) reactions of oximes. These reactions are diverse in nature and have been employed for syntheses of oxime-based metal complexes and cage-compounds, oxime functionalizations, and the preparation of new classes of organic species, in particular, a wide variety of heterocyclic systems spanning small 3-membered ring systems to macroheterocycles. This consideration gives a general outlook of reaction routes, mechanisms, and driving forces and underlines the potential of metal-involving conversions of oxime species for application in various fields of chemistry and draws attention to the emerging putative targets.

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Section: Metal-mediated Generation Of Oximesmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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“…The asymmetric nitro‐Mannich reaction of isatin ketimines with methyl 4‐nitrobutanoate 193 is best realized using the copper complex of bisoxazoline 194 (Scheme ) . The modest distereoselectivity often observed in adducts 195 is due to the limited stereocontrol on the carbon bearing the nitro group.…”

Section: Spiroheterocyclic Derivativesmentioning

confidence: 99%

Recent Developments in the Stereoselective Synthesis of Nitrogen‐Containing Heterocycles using N‐Acylimines as Reactive Substrates

Marcantoni

Petrini

2016

Adv Synth Catal

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Scheme 3. Enantioselective synthesis of trans-aziridines 8 catalyzed by chiral phosphoric acid 10. Scheme 4. Enantioselective synthesis of trans-aziridines 14. Scheme5.Preparation of chiral aziridines 17. Scheme6.Synthesis of chiral aziridines 20. Scheme 22. Synthesis of chiral 2-pyrrolines 82. Scheme23. Enantioselective synthesis of epi-cytoxazone 89. Scheme 24. Synthesis of the mGluR5modulator 96. Scheme 25. Synthesis of chiral 1,3-oxazolines. Scheme26. Synthesis of chiral imidazolidin-2-one 102. Scheme 27. Enantioselectiven itro-Mannichr eaction.Scheme28. Synthesis of (À)-nutlin-3 111.Scheme29. Synthesis of functionalized tetrahydropyridines. Scheme 32. Synthesis of chiral piperidines 129. Scheme 33. One-pot synthesis of N-formylpiperidines. Scheme34. Synthesis of bicyclic aminal 136. Scheme 39. General synthesis of isatin ketimines. Scheme 40. Asymmetric Staudinger reaction. Scheme41. Synthesis of spirocyclic oxindolo-g-lactams. Scheme 42. Synthesis of methylidenes pirocyclic compounds. Scheme 43. Synthesis of spirooxindolepyrrolines. Scheme44. Synthesis of imidazoline-based spirooxindoles. Scheme 48. Synthesis of spirolactam derivatives. Scheme49. Synthesis of spirooxindolelactams 201. Scheme50. Synthesis of polycyclic spirolactams 203. Scheme 56. Synthesis of chiral spiroazetidin-2-ones 228.

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“…For example, Pedro developed an aza-Henry reaction between isatin ketimines and 4-nitrobutyrate catalysed by a Cu(II)-Box system, which could be deprotected to undergo spontaneous cyclisation to the 3,2′-spiropiperidine oxindole (Scheme 75). 380 Hajra described an organocatalytic addition of a nitroalkyl goup followed by intramolecular alkylation (Scheme 52). 245 Meng and Li, and more recently Nakamura, reported enantioselective vinylogous Mannich reactions to generate intermediates which could be deprotected and cyclised to spirolactam products (Scheme 75).…”

Section: Spiropiperidinyl Oxindolesmentioning

confidence: 99%