4,4′-disubstituted BINAPs for highly enantioselective Ru-catalyzed asymmetric hydrogenation of ketones

被引：64
|
作者：
Hu, AG [1 ]
Ngo, HL [1 ]
Lin, WB [1 ]
机构：
[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
来源：
ORGANIC LETTERS | 2004年 / 6卷 / 17期
关键词：
D O I：
10.1021/ol048993j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A family of tunable precatalysts Ru(4,4'-BINAP)(chiral diamine)Cl-2 was synthesized and used for highly enantioselective hydrogenation of aromatic ketones. This result differs from previous chiral diphosphines that rely on the bis(xylyl)phosphino groups to control enantioselectivity. An X-ray structural study reveals that the bulky substituents on the 4,4'-positions of BINAP can effectively create a suitable chiral pocket in the transition state and thus provide a new mechanism for the enantiocontrol in such a remarkable asymmetric catalytic process.
引用
收藏
页码：2937 / 2940
页数：4
相关论文
共 50 条
  • [41] Palladium-catalyzed intermolecular asymmetric hydroamination with 4,4′-disubstituted BINAP and SEGPHOS
    Hu, Aiguo
    Ogasawara, Masamichi
    Sakamoto, Takeshi
    Okada, Atsushi
    Nakajima, Kiyohiko
    Takahashi, Tamotsu
    Lin, Wenbin
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2051 - 2056
  • [42] Carbohydrate-based pseudo-dipeptides: new ligands for the highly enantioselective Ru-catalyzed transfer hydrogenation reaction
    Coll, Mercedes
    Pamies, Oscar
    Adolfsson, Hans
    Dieguez, Montserrat
    CHEMICAL COMMUNICATIONS, 2011, 47 (44) : 12188 - 12190
  • [43] Highly effective chiral dipyridylphosphine ligands: Synthesis, structural determination, and applications in the Ru-catalyzed asymmetric hydrogenation reactions
    Pai, CC
    Lin, CW
    Lin, CC
    Chen, CC
    Chan, ASC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11513 - 11514
  • [44] 4,4′-disubstituted L-prolines as highly enantioselective catalysts for direct aldol reactions
    Gu, Liuqun
    Yu, Menglong
    Wu, Xiaoyu
    Zhang, Yazhu
    Zhao, Gang
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2223 - 2228
  • [45] Mechanism and Origin of Chemoselectivity of Ru-Catalyzed Cross-Coupling of Secondary Alcohols to β-Disubstituted Ketones
    Liu, Tian-Tian
    Tang, Shi-Ya
    Hu, Bing
    Liu, Peng
    Bi, Siwei
    Jiang, Yuan-Ye
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19): : 12444 - 12455
  • [46] Enantioselective Synthesis of trans-Disubstituted Cyclopropyltrifluoroborate Building Blocks through Ru-Catalyzed Cyclopropanation
    Nguyen, Thach
    Sreekumar, Sanil
    Wang, Shuai
    Jiang, Qi
    Montel, Florian
    Buono, Frederic
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (11) : 2979 - 2985
  • [47] Ir- and Ru-catalyzed sequential reactions:: Asymmetric α-alkylative reduction of ketones with alcohols
    Onodera, Gen
    Nishibayashi, Yoshiaki
    Uemura, Sakae
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (23) : 3819 - 3822
  • [48] Enantioselective Transfer Hydrogenation of Aromatic Ketones Catalyzed by New Diaminodiphosphine Ru(Ⅱ) Complexes
    XU Pian pian
    Chemical Research in Chinese Universities, 1998, (03) : 118 - 121
  • [49] Synthesis and structural characterization of a highly effective chiral dipyridylphosphine ligand and its application in the Ru-catalyzed asymmetric hydrogenation of β-ketoesters
    Wu, J
    Chen, H
    Zhou, ZY
    Yeung, CH
    Chan, ASC
    SYNLETT, 2001, : 1050 - 1054
  • [50] Highly efficient synthesis of chiral aromatic ketones via Rh-catalyzed asymmetric hydrogenation of β,β-disubstituted enones
    Zhang, Tao
    Jiang, Jun
    Yao, Lin
    Geng, Huiling
    Zhang, Xumu
    CHEMICAL COMMUNICATIONS, 2017, 53 (66) : 9258 - 9261
12345