Enantiopure Cyclic Nitrones: A Useful Class of Building Blocks for Asymmetric Syntheses

Revuelta, Julia; Cicchi, Stefano; Goti, Andrea; Brandi, Alberto

doi:10.1055/s-2007-965914

Cited by 30 publications

(2 citation statements)

References 65 publications

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“…During the last few decades carbohydrate-derived nitrones have turned out to be particularly attractive tools for the synthesis of structurally complex compounds [1–4]. Employed mainly as 1,3-dipoles in cycloadditions [5–6] or as imine analogues in nucleophilic additions [7–8], these nitrones very often furnish the corresponding products in a highly selective manner.…”

Section: Introductionmentioning

confidence: 99%

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

Jasiński

Lentz

Reißig

2012

Beilstein J. Org. Chem.

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SummaryAn approach to enantiopure hydroxylated 2H-1,2-oxazine derivatives is presented utilizing the [3 + 3] cyclisation of lithiated alkoxyallenes and an L-erythrose-derived N-glycosyl nitrone as precursors. This key step proceeded only with moderate diastereoselectivity, but allowed entry into both enantiomeric series of the resulting 3,6-dihydro-2H-1,2-oxazines. Their enol ether double bond was then subjected to a hydroboration followed by an oxidative work-up, and finally the auxiliary was removed. The described three-step procedure enabled the synthesis of enantiopure hydroxylated 1,2-oxazines. Typical examples were treated with samarium diiodide leading to enantiopure acyclic aminopolyols. We also report on our attempts to convert these compounds into enantiopure hydroxylated pyrrolidine derivatives.

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Section: Introductionmentioning

confidence: 99%

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

Jasiński

Lentz

Reißig

2012

Beilstein J. Org. Chem.

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“…Its multifaceted applications as spin trapping agents, bioorthogonal probes and efficacious therapeutic agents also render nitrone a heavily pursued synthetic target. Chiral nitrones also serve as important building blocks in asymmetric synthesis . In stark contrast to their versatile reactivity and prominent roles, routinely employed methods to synthesize nitrones still rely heavily on traditional strategies − (Scheme , i–iii).…”

mentioning

confidence: 99%

Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime

Zhao

Sun

et al. 2017

J. Am. Chem. Soc.

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We report realization of the first enantioselective Cope-type hydroamination of oximes for asymmetric nitrone synthesis. The ligand promoted asymmetric cyclopropene "hydronitronylation" process employs a Cu-based catalytic system and readily available starting materials, operates under mild conditions and displays broad scope and exceptionally high enantio- and diastereocontrol. Preliminary mechanistic studies corroborate a Cu-catalytic profile featuring an olefin metalla-retro-Cope aminocupration process as the key C-N bond forming event. This conceptually novel reactivity enables the first example of highly enantioselective catalytic nitrone formation process and will likely spur further developments that may significantly expedite chiral nitrone synthesis.

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Effective Oxidation of Secondary Amines to Nitrones with Alkyl Hydroperoxides Catalysed by (Trialkanolaminato)titanium(IV) Complexes

et al. 2010

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The effective catalytic oxidation of secondary amines to nitrones with alkyl hydroperoxides as the primary oxidants is described. The titanium alkoxide catalysts are protected from the water co-product by the combined use of a tightly binding trialkanolamine ligand and molecular sieves. Nitrones can be obtained in high yields (up to 98%) under homogeneous, anhydrous conditions and even in the absence of solvent. The reactions are fast (2-7 h) and good selectivity and complete conversion can be achieved with as little as 1% catalys

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Enantiopure Cyclic Nitrones: A Useful Class of Building Blocks for Asymmetric Syntheses

Cited by 30 publications

References 65 publications

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

Carbohydrate-auxiliary assisted preparation of enantiopure 1,2-oxazine derivatives and aminopolyols

Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime

Effective Oxidation of Secondary Amines to Nitrones with Alkyl Hydroperoxides Catalysed by (Trialkanolaminato)titanium(IV) Complexes

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