Dynamic kinetic resolution:: an efficient route to anti α-amino-β-hydroxy esters via Ru-SYNPHOS® catalyzed hydrogenation

被引:59
|
作者
Mordant, C [1 ]
Dünkelmann, P [1 ]
Ratovelomanana-Vidal, V [1 ]
Genet, JP [1 ]
机构
[1] Ecole Natl Super Chim Paris, CNRS, UMR 7573, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France
关键词
D O I
10.1039/b401631a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Ru(II)-catalyzed hydrogenation of alpha-amino-beta-keto esters as their hydrochloride salts affords preparation of the corresponding anti alpha-amino-beta-hydroxy esters under mild conditions with high diastereoselectivities and enantioselectivities via dynamic kinetic resolution.
引用
收藏
页码:1296 / 1297
页数:2
相关论文
共 50 条
  • [1] A versatile route to syn- and anti-α-amino β-hydroxy esters from β-keto esters by dynamic kinetic resolution with Ru-SYNPHOS® catalyst
    Mordant, C
    Dünkelmann, P
    Ratovelomanana-Vidal, V
    Genet, JP
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (14) : 3017 - 3026
  • [2] Asymmetric Synthesis of anti-β-Amino-α-Hydroxy Esters via Dynamic Kinetic Resolution of β-Amino-α-Keto Esters
    Goodman, C. Guy
    Do, Dung T.
    Johnson, Jeffrey S.
    ORGANIC LETTERS, 2013, 15 (10) : 2446 - 2449
  • [3] Catalytic anti-Selective Asymmetric Hydrogenation of α-Amino-β-Keto Esters through Dynamic Kinetic Resolution
    Hamada, Yasumasa
    Makino, Kazuishi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2008, 66 (11) : 1057 - 1065
  • [4] Iridium-SYNPHOS-Catalyzed Hydrogenation through Dynamic Kinetic Resolution of α-Amino β-Keto Ester Hydrochlorides
    Echeverria, Pierre-Georges
    Ferard, Charlene
    Cornil, Johan
    Guerinot, Amandine
    Cossy, Janine
    Phansavath, Phannarath
    Ratovelomanana-Vidal, Virginie
    SYNLETT, 2014, 25 (19) : 2761 - 2764
  • [5] Synthesis and Application of Chiral Ru Pincer Catalysts on the Hydrogenation of α-Hydroxy Esters by Dynamic Kinetic Resolution
    Wang, Biwen
    Du, Tian
    Tang, Weijun
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2020, 41 (10): : 2256 - 2263
  • [6] Dynamic kinetic resolution of β′-keto-β-amino esters using Ru-DTBM-Sunphos catalyzed asymmetric hydrogenation
    Li, Xiaoming
    Tao, Xiaoming
    Ma, Xin
    Li, Wanfang
    Zhao, Mengmeng
    Xie, Xiaomin
    Ayad, Tahar
    Ratovelomanana-Vidal, Virginie
    Zhang, Zhaoguo
    TETRAHEDRON, 2013, 69 (34) : 7152 - 7156
  • [7] 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
  • [8] Efficient lipase-catalyzed kinetic resolution and dynamic kinetic resolution of β-hydroxy nitriles.: A route to useful precursors for γ-amino alcohols
    Pàmies, O
    Bäckvall, JE
    ADVANCED SYNTHESIS & CATALYSIS, 2001, 343 (6-7) : 726 - 731
  • [9] Enzymatic kinetic resolution and chemoenzymatic dynamic kinetic resolution of δ-hydroxy esters.: An efficient route to chiral δ-lactones
    Pàmies, O
    Bäckvall, JE
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04): : 1261 - 1265
  • [10] Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts-stereoselective synthesis of anti-β-hydroxy-α-amino acids
    Makino, Kazuishi
    Goto, Takayuki
    Hiroki, Yasuhiro
    Hamada, Yasumasa
    TETRAHEDRON-ASYMMETRY, 2008, 19 (24) : 2816 - 2828