Rhodium-catalyzed asymmetric hydrogenation of unprotected β-enamine phosphonates

被引:11
|
作者
Zhou, Ming [1 ]
Xue, Zejian [1 ]
Cao, Min [1 ]
Dong, Xiu-Qin [1 ]
Zhang, Xumu [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA-AMINO; AMINOPHOSPHONATES; INHIBITOR;
D O I
10.1039/c6ob00540c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have successfully developed a strategy for the first time for the enantioselective Rh-TaniaPhos catalyzed asymmetric hydrogenation of unprotected beta-enamine phosphonates to free beta-amino phosphonates directly with good enantioselectivities (80%-86% ee) and high conversions (>99% conversion). The resulting chiral free beta-amino phosphonates and their derivatives are important intermediates in biochemistry and pharmaceuticals.
引用
收藏
页码:4582 / 4584
页数:3
相关论文
共 50 条
  • [31] PipPhos and MorfPhos: Privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation
    Bernsmann, H
    van den Berg, M
    Hoen, R
    Minnaard, AJ
    Mehler, G
    Reetz, MT
    De Vries, JG
    Feringa, BL
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03): : 943 - 951
  • [32] Carboranylphosphites - new effective ligands for rhodium-catalyzed asymmetric hydrogenation of dimethyl itaconate
    Lyubimov, Sergey E.
    Tyutyunov, Andrey A.
    Kalinin, Valery N.
    Said-Galiev, Ernest E.
    Khokhlov, Alexey R.
    Petrovskii, Pavel V.
    Davankov, Vadim A.
    TETRAHEDRON LETTERS, 2007, 48 (46) : 8217 - 8219
  • [33] Marked deuterium isotope effects on the enantioselectivity in rhodium-catalyzed asymmetric hydrogenation of enamides
    Imamoto, Tsuneo
    Itoh, Takuma
    Yoshida, Kazuhiro
    Gridnev, Ilya D.
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1636 - 1641
  • [34] Rhodium-catalyzed asymmetric hydrogenation with self-assembling catalysts in propylene carbonate
    Schaeffner, Benjamin
    Hoiz, Jens
    Verevkin, Sergey P.
    Boerner, Armin
    TETRAHEDRON LETTERS, 2008, 49 (05) : 768 - 771
  • [35] Origin of the Selectivity and Activity in the Rhodium-Catalyzed Asymmetric Hydrogenation Using Supramolecular Ligands
    Daubignard, Julien
    Lutz, Martin
    Detz, Remko J.
    de Bruin, Bas
    Reek, Joost N. H.
    ACS CATALYSIS, 2019, 9 (08) : 7535 - 7547
  • [36] Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation
    Herseczki, Z
    Gergely, I
    Hegedüs, C
    Szöllösy, A
    Bakos, J
    TETRAHEDRON-ASYMMETRY, 2004, 15 (11) : 1673 - 1676
  • [37] Origin of enantioreversal in the rhodium-catalyzed asymmetric hydrogenation of prochiral enamides and the effect of the α-substituent
    Feldgus, S
    Landis, CR
    ORGANOMETALLICS, 2001, 20 (11) : 2374 - 2386
  • [38] OPTICALLY-ACTIVE PHENANTHROLINES IN ASYMMETRIC CATALYSIS - RHODIUM-CATALYZED ASYMMETRIC TRANSFER HYDROGENATION OF ACETOPHENONE
    GLADIALI, S
    CHELUCCI, G
    CHESSA, G
    DELOGU, G
    SOCCOLINI, F
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 327 (01) : C15 - C17
  • [39] Regiodivergence in rhodium-catalyzed asymmetric hydroboration
    Bochat, Andrew
    Shoba, Veronika
    Chakrabarty, Suman
    Hoang, Gia
    Wickrama, Rukshani
    Palencia, Hector
    Takacs, James
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [40] Chiral α-Amino Phosphonates via Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions
    Lefevre, Nicolas
    Brayer, Jean-Louis
    Folleas, Benoit
    Darses, Sylvain
    ORGANIC LETTERS, 2013, 15 (16) : 4274 - 4276