Indane

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Zhongyin Zhang - One of the best experts on this subject based on the ideXlab platform.

  • total synthesis and stereochemical assignment of delavatine a rh catalyzed asymmetric hydrogenation of indene type tetrasubstituted olefins and kinetic resolution through pd catalyzed triflamide directed c h olefination
    Journal of the American Chemical Society, 2017
    Co-Authors: Zhongyin Zhang, Jinxin Wang, Fan Yang, Guodu Liu, Wenjun Tang, Yunheng Shen, Weidong Zhang
    Abstract:

    Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of β-alkyl phenylethylamine derivatives through Pd-catalyzed triflamide-directed C–H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfonamides. The kinetic resolution provided a collection of enantioenriched Indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantiopurity. In ...

  • Total Synthesis and Stereochemical Assignment of Delavatine A: Rh-Catalyzed Asymmetric Hydrogenation of Indene-Type Tetrasubstituted Olefins and Kinetic Resolution through Pd-Catalyzed Triflamide-Directed C–H Olefination
    2017
    Co-Authors: Zhongyin Zhang, Jinxin Wang, Fan Yang, Guodu Liu, Wenjun Tang, Yunheng Shen
    Abstract:

    Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of β-alkyl phenyl­ethyl­amine derivatives through Pd-catalyzed triflamide-directed C–H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfon­amides. The kinetic resolution provided a collection of enantio­enriched Indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantio­purity. In the synthesis, the triflamide served as not only an effective directing group for C–H bond activation but also a versatile functional group for further elaborations. The relative and absolute configurations of delavatine A were unambiguously assigned by the syntheses of the natural product and its three stereo­isomers. Their cyto­toxicity against a series of cancer cell lines was evaluated

Luiz F Silva - One of the best experts on this subject based on the ideXlab platform.

  • a comparative study of thallium iii and iodine iii mediated ring contraction reactions for the synthesis of Indane
    New Journal of Chemistry, 2021
    Co-Authors: Luiz F Silva, Ajmir Khan, Muhammad Rabnawaz
    Abstract:

    Reported herein is a comparative study of the synthesis of Indane via ring contraction reaction, mediated by iodine(III) and thallium(III). A series of protected 1,2-dihydronaphthalenes were synthesized and subjected to hydroxy(tosyloxy)iodobenzene (HTIB) and thallium(III) nitrate trihydrate (TTN) in trimethyl orthoformate (TMOF) to compare the percent yields provided by both oxidizing agents. The yields of the ring contracted products (Indanes) were in the range of 61–88% for reactions performed with TTN·3H2O in TMOF. However, the yields were found to be significantly lower (e.g., 18–34%) when using HTIB in TMOF with some addition products. This study provides an important development related to the efficacy of the two oxidizing agents for ring contraction reaction.

  • Molecular conformation of the racemic indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide
    Structural Chemistry, 2009
    Co-Authors: Antonio C. Doriguetto, Fernanda A. Siqueira, Luiz F Silva, Rodrigo S. Corrêa, Javier Ellena
    Abstract:

    This paper presents the structural characterization of the indan derivative (±)-1- trans -3-(3,4-dichlorophenyl)-2,3-dihydro-1 H -indene-1-carboxamide, which was unambiguously determined by X-ray diffraction (XRD) to be a racemate (R/S: 50/50) crystallizing in an achiral crystal structure (P2_1/c, a  = 9.3180(1) Å, b  = 7.9070(2) Å, c  = 19.7550(4) Å, β = 103.250(1)°, V  = 1416.75(5) Å^3 and Z  = 4). The diastereomers are related by the inversion symmetry and linked by H bond forming a dimer. The crystal packing is stabilized by hydrogen bonds, including the classical one responsible for the formation of centrosymmetric dimers, and non-classical ones involving C–H···O and C–H···π-aryl interactions. The intra and intermolecular geometry of the title compound is compared to the (±)-1- trans -3-(3,4-dichlorophenyl)-2,3-dihydro-1 H -indene-1-carboxylic acid one, which also present an achiral crystal structure from racemates (R/S: 50/50). The two indan derivatives crystallize in a very similar unit cell.

  • molecular conformation of the racemic indan derivative 1 trans 3 3 4 dichlorophenyl 2 3 dihydro 1h indene 1 carboxamide
    Structural Chemistry, 2009
    Co-Authors: Antonio C. Doriguetto, Fernanda A. Siqueira, Luiz F Silva, Rodrigo S. Corrêa, Javier Ellena
    Abstract:

    This paper presents the structural characterization of the indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide, which was unambiguously determined by X-ray diffraction (XRD) to be a racemate (R/S: 50/50) crystallizing in an achiral crystal structure (P21/c, a = 9.3180(1) A, b = 7.9070(2) A, c = 19.7550(4) A, β = 103.250(1)°, V = 1416.75(5) A3 and Z = 4). The diastereomers are related by the inversion symmetry and linked by H bond forming a dimer. The crystal packing is stabilized by hydrogen bonds, including the classical one responsible for the formation of centrosymmetric dimers, and non-classical ones involving C–H···O and C–H···π-aryl interactions. The intra and intermolecular geometry of the title compound is compared to the (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxylic acid one, which also present an achiral crystal structure from racemates (R/S: 50/50). The two indan derivatives crystallize in a very similar unit cell.

  • Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline.
    Organic Letters, 2007
    Co-Authors: Luiz F Silva, Fernanda A. Siqueira, Eliane C. Pedrozo, Fabiana Y. M. Vieira, Antonio C. Doriguetto
    Abstract:

    A new approach for the synthesis of (±)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.

  • iodine iii promoted ring contraction of 1 2 dihydronaphthalenes a diastereoselective total synthesis of indatraline
    Organic Letters, 2007
    Co-Authors: Luiz F Silva, Fernanda A. Siqueira, Eliane C. Pedrozo, Fabiana Y. M. Vieira, Antonio C. Doriguetto
    Abstract:

    A new approach for the synthesis of (±)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.

Jinxin Wang - One of the best experts on this subject based on the ideXlab platform.

  • total synthesis and stereochemical assignment of delavatine a rh catalyzed asymmetric hydrogenation of indene type tetrasubstituted olefins and kinetic resolution through pd catalyzed triflamide directed c h olefination
    Journal of the American Chemical Society, 2017
    Co-Authors: Zhongyin Zhang, Jinxin Wang, Fan Yang, Guodu Liu, Wenjun Tang, Yunheng Shen, Weidong Zhang
    Abstract:

    Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of β-alkyl phenylethylamine derivatives through Pd-catalyzed triflamide-directed C–H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfonamides. The kinetic resolution provided a collection of enantioenriched Indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantiopurity. In ...

  • Total Synthesis and Stereochemical Assignment of Delavatine A: Rh-Catalyzed Asymmetric Hydrogenation of Indene-Type Tetrasubstituted Olefins and Kinetic Resolution through Pd-Catalyzed Triflamide-Directed C–H Olefination
    2017
    Co-Authors: Zhongyin Zhang, Jinxin Wang, Fan Yang, Guodu Liu, Wenjun Tang, Yunheng Shen
    Abstract:

    Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of β-alkyl phenyl­ethyl­amine derivatives through Pd-catalyzed triflamide-directed C–H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfon­amides. The kinetic resolution provided a collection of enantio­enriched Indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantio­purity. In the synthesis, the triflamide served as not only an effective directing group for C–H bond activation but also a versatile functional group for further elaborations. The relative and absolute configurations of delavatine A were unambiguously assigned by the syntheses of the natural product and its three stereo­isomers. Their cyto­toxicity against a series of cancer cell lines was evaluated

Antonio C. Doriguetto - One of the best experts on this subject based on the ideXlab platform.

  • Molecular conformation of the racemic indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide
    Structural Chemistry, 2009
    Co-Authors: Antonio C. Doriguetto, Fernanda A. Siqueira, Luiz F Silva, Rodrigo S. Corrêa, Javier Ellena
    Abstract:

    This paper presents the structural characterization of the indan derivative (±)-1- trans -3-(3,4-dichlorophenyl)-2,3-dihydro-1 H -indene-1-carboxamide, which was unambiguously determined by X-ray diffraction (XRD) to be a racemate (R/S: 50/50) crystallizing in an achiral crystal structure (P2_1/c, a  = 9.3180(1) Å, b  = 7.9070(2) Å, c  = 19.7550(4) Å, β = 103.250(1)°, V  = 1416.75(5) Å^3 and Z  = 4). The diastereomers are related by the inversion symmetry and linked by H bond forming a dimer. The crystal packing is stabilized by hydrogen bonds, including the classical one responsible for the formation of centrosymmetric dimers, and non-classical ones involving C–H···O and C–H···π-aryl interactions. The intra and intermolecular geometry of the title compound is compared to the (±)-1- trans -3-(3,4-dichlorophenyl)-2,3-dihydro-1 H -indene-1-carboxylic acid one, which also present an achiral crystal structure from racemates (R/S: 50/50). The two indan derivatives crystallize in a very similar unit cell.

  • molecular conformation of the racemic indan derivative 1 trans 3 3 4 dichlorophenyl 2 3 dihydro 1h indene 1 carboxamide
    Structural Chemistry, 2009
    Co-Authors: Antonio C. Doriguetto, Fernanda A. Siqueira, Luiz F Silva, Rodrigo S. Corrêa, Javier Ellena
    Abstract:

    This paper presents the structural characterization of the indan derivative (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxamide, which was unambiguously determined by X-ray diffraction (XRD) to be a racemate (R/S: 50/50) crystallizing in an achiral crystal structure (P21/c, a = 9.3180(1) A, b = 7.9070(2) A, c = 19.7550(4) A, β = 103.250(1)°, V = 1416.75(5) A3 and Z = 4). The diastereomers are related by the inversion symmetry and linked by H bond forming a dimer. The crystal packing is stabilized by hydrogen bonds, including the classical one responsible for the formation of centrosymmetric dimers, and non-classical ones involving C–H···O and C–H···π-aryl interactions. The intra and intermolecular geometry of the title compound is compared to the (±)-1-trans-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene-1-carboxylic acid one, which also present an achiral crystal structure from racemates (R/S: 50/50). The two indan derivatives crystallize in a very similar unit cell.

  • Iodine(III)-promoted ring contraction of 1,2-dihydronaphthalenes: a diastereoselective total synthesis of (+/-)-indatraline.
    Organic Letters, 2007
    Co-Authors: Luiz F Silva, Fernanda A. Siqueira, Eliane C. Pedrozo, Fabiana Y. M. Vieira, Antonio C. Doriguetto
    Abstract:

    A new approach for the synthesis of (±)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.

  • iodine iii promoted ring contraction of 1 2 dihydronaphthalenes a diastereoselective total synthesis of indatraline
    Organic Letters, 2007
    Co-Authors: Luiz F Silva, Fernanda A. Siqueira, Eliane C. Pedrozo, Fabiana Y. M. Vieira, Antonio C. Doriguetto
    Abstract:

    A new approach for the synthesis of (±)-indatraline, which is a 3-phenyl-1-indanamine that displays several biological activities, is described. The strategy features as the key step a diastereoselective ring contraction of a 1,2-dihydronaphthalene promoted by PhI(OTs)OH, to construct the indan ring system. The oxidative rearrangement of other 1,2-dihydronaphthalenes was also investigated, generalizing this method to obtain indans.

Weidong Zhang - One of the best experts on this subject based on the ideXlab platform.

  • total synthesis and stereochemical assignment of delavatine a rh catalyzed asymmetric hydrogenation of indene type tetrasubstituted olefins and kinetic resolution through pd catalyzed triflamide directed c h olefination
    Journal of the American Chemical Society, 2017
    Co-Authors: Zhongyin Zhang, Jinxin Wang, Fan Yang, Guodu Liu, Wenjun Tang, Yunheng Shen, Weidong Zhang
    Abstract:

    Delavatine A (1) is a structurally unusual isoquinoline alkaloid isolated from Incarvillea delavayi. The first and gram-scale total synthesis of 1 was accomplished in 13 steps (the longest linear sequence) from commercially available starting materials. We exploited an isoquinoline construction strategy and developed two reactions, namely Rh-catalyzed asymmetric hydrogenation of indene-type tetrasubstituted olefins and kinetic resolution of β-alkyl phenylethylamine derivatives through Pd-catalyzed triflamide-directed C–H olefination. The substrate scope of the first reaction covered unfunctionalized olefins and those containing polar functionalities such as sulfonamides. The kinetic resolution provided a collection of enantioenriched Indane- and tetralin-based triflamides, including those bearing quaternary chiral centers. The selectivity factor (s) exceeded 100 for a number of substrates. These reactions enabled two different yet related approaches to a key intermediate 28 in excellent enantiopurity. In ...