Transition-Metal-Catalyzed Ring Expansion of Diazocarbonylated Cyclic <i>N</i>-Hydroxylamines: A New Approach to Cyclic Ketonitrones

Kui, Evelyn Lieou; Kanazawa, Alice; Poisson, Jean‐François; Py, Sandrine

doi:10.1021/ol502029z

Cited by 11 publications

(3 citation statements)

References 48 publications

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“…Synthesis employing 1,3‐DCA of nitrones in the preparation of ring‐junction substituted polyhydroxy indolizidines was also reported by Lieou Kui and coworkers [119] two years later (Scheme 24). Ketonitrone 146 was prepared in two steps [120–121] from L‐xylose derived aldonitrone 145 . 1,3‐DCA of ketonitrone 146 to 3‐buten‐1‐ol afforded a mixture of exo‐anti ( 147 a ) and endo‐anti ( 147 b ) isoxazolidines with a diastereomeric ratio 85 : 15.…”

Section: Synthesis and Inhibitory Activity Of New Indolizidine Iminos...mentioning

confidence: 99%

Recent Developments in the Synthesis of Polyhydroxylated Indolizidines

Fraňová

Marchalı́n

2022

Eur J Org Chem

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Since their discovery, polyhydroxylated indolizidines have been the focus of attention for both biologists and synthetic chemists. They are classified as iminosugar alkaloids: nitrogenbased carbohydrate mimetics that are potent inhibitors of glycosidases. Many discovered glycosidase inhibitors were found to possess biological activity, and they are therefore considered to be potential therapeutics in the treatment of various diseases such as viral infections, diabetes, or cancer. Not surprisingly, the interest in the preparation of these substances has been enormous. This review presents the latest developments in the synthesis of naturally occurring polyhydroxylated indolizidines and their synthetic enantiomers. In addition, the synthesis of several novel polyhydroxylated indolizidines, which were discovered to have inhibitory activity, is reported.

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Section: Synthesis and Inhibitory Activity Of New Indolizidine Iminos...mentioning

confidence: 99%

Recent Developments in the Synthesis of Polyhydroxylated Indolizidines

Fraňová

Marchalı́n

2022

Eur J Org Chem

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“…[61] On the other hand, the addition to cyclic nitrones proceeded quantitatively and with complete selectivity, only one isomer being isolated from the reaction mixture. [62] The addition of a lithiated purine to cyclic nitrones also proceeded with total selectivity. The resulting hydroxylamine was used for the preparation of analogs of forodesine, a human purine nucleoside phosphorylase inhibitor.…”

Section: Organolithium Compoundsmentioning

confidence: 99%

Recent Advances in the Preparation of Enantiomerically Pure Hydroxylamines from Nitrones

Matute¹,

García‐Viñuales²,

Hayes³

et al. 2016

COS

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This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Addition of carbanions derived from enolates, cyanide or fluorinated derivatives allow the preparation of complex structures. Radical additions and, in particular samarium diiodide-mediated reductive coupling of nitrones with carbonyl compounds and α,β-unsaturated esters have also been considered. All these approaches provide efficient methods of preparation of enantiomerically pure hydroxylamienes that are valuable synthetic intermediates. KeywordsHydroxylamines; Nitrones; Organometallics; Mannich; Reductive coupling 2 Graphical Abstract 3

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“…In the past few decades, the development of C–H functionalization reactions that enable the construction of fundamentally important C–C and C–X bonds has witnessed tremendous upsurge. 1–11 Within the domain, transition metal catalysis forms the largest, ever expanding subset contributing to the broad spectrum of applications that ranges from organic synthesis to petrochemical processing. 12–20 In this context, the development of novel methods to access arylation, 21–24 alkenylation 25–27 and alkynylation of C–H bonds 28 has gained tremendous attention.…”

Section: Introductionmentioning

confidence: 99%