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Allylic Amination

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Shu-li You – One of the best experts on this subject based on the ideXlab platform.

  • Iridium-Catalyzed Asymmetric Allylic Amination Reactions with N-Aryl Phosphoramidite Ligands
    Organometallics, 2016
    Co-Authors: Xiao Zhang, Qiang Cheng, Wen-bo Liu, Shu-li You
    Abstract:

    A series of N-aryl phosphoramidite ligands were synthesized, and the iridium complexes derived from these novel ligands were proven to be efficient catalysts for asymmetric intermolecular Allylic Amination reactions. This C–N bond forming process readily accommodates a diverse range of amines and Allylic carbonates, especially for the previously challenging ortho-substituted cinnamyl substrates. Moreover, isolation and characterization of the corresponding (π-allyl)–iridium complex K1 reveal that the active iridacycle is generated through a C(sp2)–H bond insertion of tetrahydroquinoline of the ligand.

  • Enantioselective Synthesis of Pyrrole-Fused Piperazine and Piperazinone Derivatives via Ir-Catalyzed Asymmetric Allylic Amination
    ACS Catalysis, 2016
    Co-Authors: Chun-xiang Zhuo, Xiao Zhang, Shu-li You
    Abstract:

    Ir-catalyzed intramolecular asymmetric Allylic Amination reaction of pyrrole derivatives was achieved. The pyrrole-fused piperazine and piperazinone derivatives could be easily accessed from the pyrrole-tethered Allylic carbonates in good yields and enantioselectivity (up to 98% ee).

  • Highly Regio‐ and Enantioselective Synthesis of N‐Substituted 2‐Pyridones: Iridium‐Catalyzed Intermolecular Asymmetric Allylic Amination.
    ChemInform, 2015
    Co-Authors: Xiao Zhang, Ze-peng Yang, Lin Huang, Shu-li You
    Abstract:

    The Ir-catalyzed asymmetric Allylic Amination of 2-hydroxypyridines with allyl methyl carbonates (II) is reported for the first time.

Toshiyuki Itoh – One of the best experts on this subject based on the ideXlab platform.

  • Enantioselective Allylic Amination of Trifluoromethyl Group Substituted Racemic and Unsymmetrical 1,3-Disubstituted Allylic Esters by Palladium Catalysts.
    ChemInform, 2014
    Co-Authors: Motoi Kawatsura, Shou Terasaki, Maki Minakawa, Takuya Hirakawa, Kazunori Ikeda, Toshiyuki Itoh
    Abstract:

    A facile protocol for the regio- and enantioselective Allylic Amination of Allylic esters to give the corresponding α-type Allylic amines is presented.

  • Enantioselective Allylic Amination of Trifluoromethyl Group Substituted Racemic and Unsymmetrical 1,3-Disubstituted Allylic Esters by Palladium Catalysts
    Organic letters, 2014
    Co-Authors: Motoi Kawatsura, Shou Terasaki, Maki Minakawa, Takuya Hirakawa, Kazunori Ikeda, Toshiyuki Itoh
    Abstract:

    The palladium-catalyzed regio- and enantioselective Allylic Amination of trifluoromethyl group substituted racemic and unsymmetrical 1,3-disubstituted Allylic esters has been accomplished. The enantioselective formation of the α-type Allylic amines was attained by the dynamic kinetic asymmetric transformation (DYKAT).

  • Ruthenium-catalyzed regio- and enantioselective Allylic Amination of racemic 1-arylallyl esters.
    Organic letters, 2014
    Co-Authors: Motoi Kawatsura, Shou Terasaki, Kenta Uchida, Hiroaki Tsuji, Maki Minakawa, Toshiyuki Itoh
    Abstract:

    The regio- and enantioselective Allylic Amination of racemic monosubstituted Allylic esters, such as 1-arylallyl acetates, with cyclic secondary amines has been accomplished. The RuCl3/(S,S)-ip-pybox catalyst system has effectively catalyzed the reaction to afford the enantiomerically enriched branch-type Allylic amines with perfect regioselectivity and high enantioselectivity.

Motoi Kawatsura – One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of α-Tertiary Amines by the Ruthenium-catalyzed Regioselective Allylic Amination of Tertiary Allylic Esters
    Chemistry Letters, 2020
    Co-Authors: Shota Mizuno, Hiroaki Tsuji, Yasuhiro Uozumi, Motoi Kawatsura
    Abstract:

    We demonstrated a ruthenium-catalyzed regioselective Allylic Amination of tertiary Allylic esters with various amines using [Cp*Ru(CH3CN)3][PF6]/5,5′-dimethyl-2,2′-bipyridine (5,5′-diMe-2,2′-bpy) a…

  • Ruthenium-catalyzed regioselective Allylic Amination of 2,3,3-trifluoroAllylic carbonates
    Organic & biomolecular chemistry, 2017
    Co-Authors: Shin-ichi Isobe, Shou Terasaki, Taisyun Hanakawa, Shota Mizuno, Motoi Kawatsura
    Abstract:

    We demonstrated the ruthenium-catalyzed Allylic Amination of 2,3,3-trifluoroAllylic carbonates with several types of amines. The reactions proceeded with several types of amines, and succeeded in obtaining polyfluorinated terminal alkenes possessing branched Allylic amines as a single regioisomer.

  • Regioselective Construction of α,α-Disubstituted Allylic Amines by the Ruthenium-Catalyzed Allylic Amination of Tertiary Allylic Acetates
    , 2017
    Co-Authors: Shota Mizuno, Shou Terasaki, Toru Shinozawa, Motoi Kawatsura
    Abstract:

    The ruthenium-catalyzed regioselective Allylic Amination of tertiary Allylic acetates with several types of amines has been accomplished. The reaction was effectively catalyzed by Cp*RuCl2/5,5′-dimethyl-2,2′-bipyridine or its related ruthenium catalyst systems, and α,α-disubstituted Allylic amines were formed as a single regioisomer in moderate to high yields

Min Shi – One of the best experts on this subject based on the ideXlab platform.

  • cinchona alkaloid catalyzed regio and enantioselective Allylic Amination of morita baylis hillman carbonates with isatins
    ChemInform, 2012
    Co-Authors: Min Shi, Meixin Zhao, Mingxiao Chen, Wenhao Tang, Dengke Wei, Tonglei Dai
    Abstract:

    The Allylic Amination products are obtained with good yields and enantioselectivities using (DHQD)2-PHAL as a catalyst.

  • Cinchona Alkaloid Catalyzed Regio‐ and Enantioselective Allylic Amination of Morita—Baylis—Hillman Carbonates with Isatins.
    ChemInform, 2012
    Co-Authors: Mei‐xin Zhao, Ming‐xiao Chen, Wen‐hao Tang, Deng‐ke Wei, Tong‐lei Dai, Min Shi
    Abstract:

    The Allylic Amination products are obtained with good yields and enantioselectivities using (DHQD)2-PHAL as a catalyst.

  • cinchona alkaloid catalyzed regio and enantioselective Allylic Amination of morita baylis hillman carbonates with isatins
    European Journal of Organic Chemistry, 2012
    Co-Authors: Min Shi, Meixin Zhao, Mingxiao Chen, Wenhao Tang, Dengke Wei, Tonglei Dai
    Abstract:

    An efficient enantioselective Allylic Amination of Morita–Baylis–Hillman (MBH) carbonates derived from methyl acrylate and aromatic aldehydes with isatins has been realized in the presence of commercially available cinchona alkaloids. The Allylic Amination products were obtained in moderate-to-good yields (46–74 %) with moderate-to-good enantioselectivities (up to 89 % ee) under mild conditions. The synthetic utility of the Amination products has been well demonstrated by the facile synthesis of methyl (3R,4R)-10-oxo-4-phenyl-2,3,4,10-tetrahydropyrimido[1,2-a]indole-3-carboxylate.

Uttam K. Tambar – One of the best experts on this subject based on the ideXlab platform.

  • Catalytic Enantioselective Allylic Amination of Olefins for the Synthesis of ent‐Sitagliptin.
    ChemInform, 2014
    Co-Authors: Hongli Bao, Liela Bayeh, Uttam K. Tambar
    Abstract:

    A two-step ene-reaction/[2,3]-rearrangement for the enantioselective Allylic Amination of nonactivated olefins is developed.

  • Catalytic Enantioselective Allylic Amination of Olefins for the Synthesis of ent-Sitagliptin.
    Synlett : accounts and rapid communications in synthetic organic chemistry, 2013
    Co-Authors: Hongli Bao, Liela Bayeh, Uttam K. Tambar
    Abstract:

    The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantiomerically enriched amines. Current methods are based on multistep transformations of functionalized Allylic electrophiles to form chiral Allylic amines. The enantioselective Allylic Amination of nonactivated olefins would represent a more direct and more attractive strategy. We report the enantio­selective synthesis of ent-sitagliptin through an Allylic Amination of a nonactivated terminal olefin.

  • catalytic enantioselective Allylic Amination of unactivated terminal olefins via an ene reaction 2 3 rearrangement
    ChemInform, 2013
    Co-Authors: Uttam K. Tambar
    Abstract:

    That is the first asymmetric Allylic Amination of unfunctionalized alkenes using a nitrogen-containing reagent and a chiral Pd-catalyst.