Asymmetric Hydrogenation of α,α′-Disubstituted Cycloketones through Dynamic Kinetic Resolution: An Efficient Construction of Chiral Diols with Three Contiguous Stereocenters

被引：79
|
作者：
Liu, Chong [1 ,2 ]
Xie, Jian-Hua [1 ,2 ]
Li, Ya-Li [1 ,2 ]
Chen, Ji-Qiang [1 ,2 ]
Zhou, Qi-Lin [1 ,2 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 02期
基金：
中国国家自然科学基金;
关键词：
asymmetric hydrogenation; cycloketones; dynamic kinetic resolution; lycorane; ruthenium; BETA-ARYLOXY ALCOHOLS; ENANTIOSELECTIVE SYNTHESIS; CATALYTIC-HYDROGENATION; PHOSPHORUS LIGANDS; RUTHENIUM; ESTERS; KETONES; CYCLIZATION; REDUCTION; COMPLEXES;
D O I：
10.1002/anie.201207561
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral diols with three contiguous stereocenters were synthesized by a highly enantioselective ruthenium-catalyzed asymmetric hydrogenation of racemic α,α′-disubstituted cycloketones involving dynamic kinetic resolution. This new catalytic asymmetric method provides a concise route to the alkaloid (+)-γ-lycorane. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：593 / 596
页数：4
相关论文
共 50 条
  • [31] Recent Progress and Applications of Transition-Metal-Catalyzed Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution
    Betancourt, Ricardo Molina
    Echeverria, Pierre-Georges
    Ayad, Tahar
    Phansavath, Phannarath
    Ratovelomanana-Vidal, Virginie
    SYNTHESIS-STUTTGART, 2021, 53 (01): : 30 - 50
  • [32] Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: hemisynthesis of Taxotere® through Ru-DIFLUORPHOS asymmetric hydrogenation
    Prevost, Sebastien
    Gauthier, Sebastien
    de Andrade, Maria Cristina Cano
    Mordant, Celine
    Touati, Ali Rhida
    Lesot, Philippe
    Savignac, Philippe
    Ayad, Tahar
    Phansavath, Phannarath
    Ratovelomanana-Vidal, Virginie
    Genet, Jean-Pierre
    TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1436 - 1446
  • [33] Rhodium-catalyzed asymmetric hydrogenation through dynamic kinetic resolution:: asymmetric synthesis of anti-β-hydroxy-α-amino acid esters
    Makino, K
    Fujii, T
    Hamada, Y
    TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 481 - 485
  • [34] Rhodium-Catalyzed Asymmetric Conjugate Addition to γ-Substituted α,β-Unsaturated γ-Lactams through Dynamic Kinetic Resolution: Asymmetric Synthesis of trans-β,γ-Disubstituted γ-Lactams
    Yan, Yu
    Li, Wen-Cong
    Meng, He
    Chen, Shufeng
    Ming, Jialin
    Hayashi, Tamio
    ACS CATALYSIS, 2023, 13 (10) : 6603 - 6609
  • [35] Highly efficient synthesis of enantioenriched vicinal halohydrins via Ir-catalyzed asymmetric hydrogenation using dynamic kinetic resolution
    He, Bin
    Chen, Gen-Qiang
    Zhang, Xumu
    CHEMICAL COMMUNICATIONS, 2024, 60 (72) : 9785 - 9788
  • [36] Highly efficient asymmetric reduction of arylpropionic aldehydes by Horse Liver Alcohol Dehydrogenase through dynamic kinetic resolution
    Giacomini, Daria
    Galletti, Paola
    Quintavalla, Arianna
    Gucciardo, Gabriele
    Paradisi, Francesca
    CHEMICAL COMMUNICATIONS, 2007, (39) : 4038 - 4040
  • [37] Stereoarrayed 2,3-Disubstituted 1-Indanols via Ruthenium(II)-Catalyzed Dynamic Kinetic Resolution-Asymmetric Transfer Hydrogenation
    Cotman, Andrei Emanuel
    Modec, Barbara
    Mohar, Barbara
    ORGANIC LETTERS, 2018, 20 (10) : 2921 - 2924
  • [38] Asymmetric Transfer Hydrogenation of rac-α-(Purin-9-yl)cyclopentones via Dynamic Kinetic Resolution for the Construction of Carbocyclic Nucleosides
    Zhang, Yi-Ming
    Zhang, Qi-Ying
    Wang, Dong-Chao
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC LETTERS, 2019, 21 (09) : 2998 - 3002
  • [39] Asymmetric Hydrogenation of a-Amino Esters into Optically Active β-Amino Alcohols through Dynamic Kinetic Resolution Catalyzed by Ruthenabicyclic Complexes
    Ishikawa, Hiroki
    Yurino, Taiga
    Komatsu, Ryo
    Gao, Ming-Yuan
    Arai, Noriyoshi
    Touge, Taichiro
    Matsumura, Kazuhiko
    Ohkuma, Takeshi
    ORGANIC LETTERS, 2023, 25 (13) : 2355 - 2360
  • [40] Synthesis of Chiral Dihydrobenzofurans and Phthalides by Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution: A Strategy for Total Synthesis of Daldinins A, B, and C and Concentricolide
    Fang, Lizhen
    Lyu, Qinghua
    Lu, Chenjuan
    Li, Huanhuan
    Liu, Saisai
    Han, Lili
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (20) : 3196 - 3200
12345