Application of the Intramolecular Isomerisation–Aldolisation from Allylic Alcohols and Allylic Silyl Ethers to the Synthesis of Indanones and Indenones

Petrignet, Julien; Roisnel, Thierry; Grée, René

doi:10.1002/chem.200700613

Cited by 48 publications

(30 citation statements)

References 97 publications

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“…syn-2-(Hydroxyphenylmethyl) indan-1-one 6 and anti-2-benzyl-3-hydroxyindan-1-one 8 were previously reported as products from chemical reactions. 1,8 Compound syn-2-benzyl-2,3-dihydroxyindan-1-one 7 was previously reported 6 as a detoxification product from the biotransformation of anti-(±)-2-benzylindan-1-ol anti-(±)-5 by B. cinerea. The alcohol 6 was obtained with 50% de in favour of the syn configuration in an overall yield of 3% (relative stereochemistry being assigned by correlation with 1 H and 13 C NMR data).…”

Section: Ohmentioning

confidence: 98%

“…These structures can play an important role in medicinal chemistry as they are present in various drugs or pharmaceutical compounds. 1 Specifically, (E)-2-benzylideneindan-1-one 1 has been shown to exhibit cytotoxic activity against murine P388 and L1210 leukaemic cells as well as human Molt 4/C8 and CEM Tlymphocytes. 2 Several methods for their preparation have been reported, the most classic involving as the first step the synthesis of indan-1-one moiety followed by an aldol reaction with the appropriate aldehydes.…”

Section: Introductionmentioning

confidence: 99%

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Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata

Pinedo-Rivilla

Aleu

Collado

2011

Tetrahedron: Asymmetry

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a b s t r a c tThe transformation of (E)-2-benzylideneindan-1-one 1 by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata as biocatalysts was studied. The results showed the catalytic potential of these fungi in affording several hydroxylation and reduction products, three of them reported here for the first time. The absolute configuration of enantiomerically pure 2-benzylindane derivatives was determined.

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Section: Ohmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata

Pinedo-Rivilla

Aleu

Collado

2011

Tetrahedron: Asymmetry

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“…4 That compound was obtained as a mixture of diastereoisomers 78 : 22 in favour of the anti-configuration and 61% ee.…”

Section: Scheme 2 Biotransformation Products Of Anti-(±)-2-benzylindamentioning

confidence: 99%

“…4 Thus, based on previous results, 5 we selected biocatalytic methods to pursue enantiomerically pure forms of benzylindane derivatives from the ketone (E)-2-benzylideneindan-1-one (1) in order to compare their antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea

et al. 2010

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Enantiomerically pure 2-benzylindane derivatives were prepared using biocatalytic methods and their absolute configuration determined. (1R,2S)-2-Benzylindan-1-ol ((1R,2S)-2) and (S)-2-benzylindan-1-one ((S)-3) were produced by fermenting baker's yeast. Lipase-mediated esterifications and hydrolysis of the corresponding racemic substrates gave rise to the enantiopure compounds (1S,2R)-2-benzylindan-1-ol ((1S,2R)-2) and (1R,2S)-2-benzylindan-1-ol ((1R,2S)-2), respectively. The antifungal activity of these products against two strains of the plant pathogen Botrytis cinerea was tested. The metabolism of anti-(±)-2-benzylindan-1-ol (anti-(±)-2) by B. cinerea as part of the fungal detoxification mechanism is also described and revealed interesting differences in the genome of both strains.

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“…This example demonstrates that oxidation and reduction steps can be merged to a one-pot procedure by transferring them into oxidative addition and reductive elimination using the transition metal as a reversible switch. Recently, this reaction has been integrated into a tandem isomerization-aldolization reaction which was applied to the synthesis of indanones and indenones [81] and for the transformation of vinylic furanoses into cyclopentenones [82].…”

Section: Iron Complexes As Catalytically Active Speciesmentioning

confidence: 99%

Iron Complexes in Organic Chemistry

Бауер¹,

Knölker²

2008

Iron Catalysis in Organic Chemistry

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Catalysis is an important field in both academic and industrial research because it leads to more efficient reactions in terms of energy consumption and waste production. The common feature of these processes is a catalytically active species which forms reactive intermediates by coordination of an organic ligand and thus decreases the activation energy. Formation of the product should occur with regeneration of the catalytically active species. The efficiency of the catalyst can be described by its turnover number, providing a measure of how many catalytic cycles are passed by one molecule of catalyst.For efficient regeneration, the catalyst should form only labile intermediates with the substrate. This concept can be realized using transition metal complexes because metal-ligand bonds are generally weaker than covalent bonds. The transition metals often exist in different oxidation states with only moderate differences in their oxidation potentials, thus offering the possibility of switching reversibly between the different oxidation states by redox reactions.Many transition metals have been applied as catalysts for organic reactions [1]. So far, iron has not played a dominant role in catalytic processes. Organoiron chemistry was started by the discovery of pentacarbonyliron in 1891, independently by Mond [2] and Berthelot [3]. A further milestone was the report of ferrocene in 1951 [4]. Iron catalysis came into focus by the Reppe synthesis [5]. Kochi and coworkers published in 1971 their results on the iron-catalyzed crosscoupling of Grignard reagents with organic halides [6]. However, cross-coupling reactions became popular by using the late transition metals nickel and palladium. More recently, the increasing number of reactions using catalytic amounts of iron complexes indicates a renaissance of this metal in catalysis. This chapter describes applications of iron complexes in organic chemistry and thus paves the way for an understanding of iron catalysis.

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Application of the Intramolecular Isomerisation–Aldolisation from Allylic Alcohols and Allylic Silyl Ethers to the Synthesis of Indanones and Indenones

Cited by 48 publications

References 97 publications

Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata

Asymmetric microbial conversion of (E)-2-benzylideneindan-1-one by the filamentous fungi Botrytis cinerea, Trichoderma viride, and Eutypa lata

Biocatalytic preparation and absolute configuration of enantiomerically pure fungistatic anti-2-benzylindane derivatives. Study of the detoxification mechanism by Botrytis cinerea

Iron Complexes in Organic Chemistry

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