A Convenient Synthesis of (-)-Methyl Epijasmonate

U, Jong Sun; Park, Hyun-Seok; Gupta, Sandhya; Kun, Jin

doi:10.1080/00397919708004999

Cited by 6 publications

(3 citation statements)

References 27 publications

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“…The existence of both ET and HAB processes in the rate-determining step was already proven. 4,7 Prior to ET+HAB, the substrate could give also a complex with a low-valent ruthenium species 7 (not displayed in Scheme 4).…”

Section: Mechanistic Considerationsmentioning

confidence: 99%

“…The powerful oxidant ruthenium tetroxide (RuO4) 1 is widely used to functionalize C-H bonds in various organic compounds, such as hydrocarbons, 2,3 halides, 4 ethers, 5 alcohols, 6 amines, [7][8][9][10][11][12] or amides. 13 Rarely, the oxidative attack takes place at a heteroatom, like in the transformation of sulfide into sulfone.…”

Section: Introductionmentioning

confidence: 99%

“…1 In most cases these reactions result in products that are biologically active intermediates useful in the synthesis of amino acids, fragrances and drugs. 4,7,11,12,14 Regarding the oxidation of amines, primary or secondary ones (R2CH-NH-R) are transformed by RuO4 into imines (R2C=N-R), by a formal 1,2-dehydrogenation process. 15,16 In addition, a less common 1,1dehydrogenation reaction transforms tertiary amines (R-CH2-NR2) to amides (R-CO-NR2), with iminium ions as intermediates.…”

Section: Introductionmentioning

confidence: 99%

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RuO4-Mediated oxidation of N-benzylated tertiary amines. Four- and three-membered azacycloalkanes as substrates

Florea¹,

HÃ®rtopeanu²,

Stavarache³

et al. 2018

Arkivoc

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Similarly to N-benzylpiperidine and -pyrrolidine, N-benzylazetidine underwent RuO4-catalyzed oxidation by attack at both types of N-methylene C-H bonds: endocyclic and exocyclic (benzylic). If the reaction is performed in the presence of cyanide, α-aminonitriles were obtained instead of amides. The regioselectivity (endocyclic/exocyclic) decreased constantly with the decrease of the azacycle size, from about 2 (for Nbenzylpiperidine) to about 0.6 (for N-benzylazetidine). The highest regioselectivity was found for Nbenzylaziridine, for which only products of benzylic functionalization resulted. Iminium ions, complexed to ruthenium species, were proposed as reactive intermediates during the oxidation of N-benzylated azacycloalkanes.

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Section: Mechanistic Considerationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

RuO4-Mediated oxidation of N-benzylated tertiary amines. Four- and three-membered azacycloalkanes as substrates

Florea¹,

HÃ®rtopeanu²,

Stavarache³

et al. 2018

Arkivoc

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Eine neue Variante der Claisen-Umlagerung von aus Allylmalonaten abgeleiteten Trimethylsilylketenacetalen – effiziente, hoch enantio- und diastereoselektive Synthesen von (+)-Methyldihydroepijasmonat und (+)-Methylepijasmonat

Fehr¹,

Galindo

2000

Angewandte Chemie

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Mit vollständiger Chiralitätsübertragung verläuft die Claisen‐Umlagerung der Trimethylsilyl(TMS)‐Ketenacetale, die aus den Allylmalonaten (R)‐1 (R=Pentyl, 2‐(Z)‐Pentenyl) hergestellt wurden. Diese sind ihrerseits durch enantioselektive Reduktion/Veresterung oder durch enzymatische kinetische Racematspaltung zugänglich. Die cis‐Konfiguration in (+)‐3 wurde durch eine hoch syn‐selektive Epoxidierung von (+)‐2 und eine anschließende suprafaciale 1,2‐H‐Wanderung sichergestellt.

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ChemInform Abstract: A Convenient Synthesis of (‐)‐Methyl Epijasmonate.

Park

Gupta

1997

ChemInform

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A Convenient Synthesis of (-)-Methyl Epijasmonate.-A short, enantioselective synthesis of the title "isoprostane" (XII) starting from commercially available Corey lactone aldehyde (I) is given. The key features of the sequence are the stereoselective construction of the 2,3-cis-disubstituted cyclopentanone system by hydrogenation of dienoate (IV) and the subsequent one-carbon degradation (V)→(VIII). -(U, J. S.; PARK, H. S.; GUPTA, S.; CHA, J. K.; Synth.

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A Convenient Synthesis of (-)-Methyl Epijasmonate

Cited by 6 publications

References 27 publications

RuO4-Mediated oxidation of N-benzylated tertiary amines. Four- and three-membered azacycloalkanes as substrates

RuO4-Mediated oxidation of N-benzylated tertiary amines. Four- and three-membered azacycloalkanes as substrates

Eine neue Variante der Claisen-Umlagerung von aus Allylmalonaten abgeleiteten Trimethylsilylketenacetalen – effiziente, hoch enantio- und diastereoselektive Synthesen von (+)-Methyldihydroepijasmonat und (+)-Methylepijasmonat

ChemInform Abstract: A Convenient Synthesis of (‐)‐Methyl Epijasmonate.

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