The synthesis of spirobitetraline phosphoramidite ligands and their application in rhodium-catalyzed asymmetric hydrogenation

被引：26
|
作者：
Huo, Xiang-Hong
Xie, Jian-Hua
Wang, Qiu-Shi
Zhou, Qi-Lin [1 ]
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：
ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 16期
关键词：
asymmetric catalysis; hydrogenation; monophosphoramidite; rhodium; spirobitetraline;
D O I：
10.1002/adsc.200700109
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A racemic 1,1'-spirobitetralin-8,8'-diol (SBITOL) was conveniently synthesized from 3-methoxybenzaldehyde in 26 % yield over 9 steps and resolved via its bis-(S)-camphorsulfonates. The corresponding chiral spirobitetraline monophosphoramidite ligands have been prepared and their rhodium complexes were applied in the asymmetric hydrogenation of dehydroamino esters with good to excellent enantioselectivities (up to 99.3 % ee).
引用
收藏
页码：2477 / 2484
页数：8
相关论文
共 50 条
  • [31] Attraction versus Repulsion in Rhodium-Catalyzed Asymmetric Hydrogenation
    Gridnev, Ilya D.
    CHEMCATCHEM, 2016, 8 (22) : 3463 - 3465
  • [32] Rhodium-Catalyzed Homogeneous Asymmetric Hydrogenation of Naphthol Derivatives
    Zhang, Shu-Xin
    Long, Linhong
    Li, Zeyu
    He, Yan-Mei
    Li, Shan
    Chen, Hui
    Hao, Wei
    Fan, Qing-Hua
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (06) : 5197 - 5211
  • [33] MECHANISTIC STUDIES OF RHODIUM-CATALYZED ASYMMETRIC HOMOGENEOUS HYDROGENATION
    BROWN, JM
    CHALONER, PA
    PARKER, D
    ADVANCES IN CHEMISTRY SERIES, 1982, (196): : 355 - 369
  • [34] Rhodium-catalyzed asymmetric hydrogenation of unprotected β-enamine phosphonates
    Zhou, Ming
    Xue, Zejian
    Cao, Min
    Dong, Xiu-Qin
    Zhang, Xumu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (20) : 4582 - 4584
  • [35] Ferrocenyl diphosphines containing stereogenic phosphorus atoms.: Synthesis and application in the rhodium-catalyzed asymmetric hydrogenation
    Maienza, F
    Wörle, M
    Steffanut, P
    Mezzetti, A
    Spindler, F
    ORGANOMETALLICS, 1999, 18 (06) : 1041 - 1049
  • [36] Synthesis and Resolution of 3,3′-Disubstituted xylBINAP Derivatives and Their Application in Rhodium-Catalyzed Asymmetric Hydrogenation
    Rankic, Danica A.
    Hopkins, J. Matthew
    Parvez, Masood
    Keay, Brian A.
    SYNLETT, 2009, (15) : 2513 - 2517
  • [37] Asymmetric synthesis of a new cylindrically chiral and air-stable ferrocenyldiphosphine and its application to rhodium-catalyzed asymmetric hydrogenation
    Kang, J
    Lee, JH
    Ahn, SH
    Choi, JS
    TETRAHEDRON LETTERS, 1998, 39 (31) : 5523 - 5526
  • [38] RHODIUM-CATALYZED ASYMMETRIC HYDROFORMYLATION WITH CHIRAL DIPHOSPHITE LIGANDS
    BUISMAN, GJH
    KAMER, PCJ
    VANLEEUWEN, PWNM
    TETRAHEDRON-ASYMMETRY, 1993, 4 (07) : 1625 - 1634
  • [39] CHIRAL IMINE LIGANDS - SYNTHESIS AND APPLICATIONS IN ASYMMETRIC RHODIUM-CATALYZED HYDROSILATION REACTIONS
    WRIGHT, ME
    SVEJDA, SA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 198 : 4 - ORGN
  • [40] Self-assembly of bidentate ligands for combinatorial homogeneous catalysis: Asymmetric rhodium-catalyzed hydrogenation
    Weis, M
    Waloch, C
    Seiche, W
    Breit, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) : 4188 - 4189
12345