Kinetic Resolution of 1,1′-Biaryl-2,2′-Diols and Amino Alcohols through NHC-Catalyzed Atroposelective Acylation

被引：187
作者：
Lu, Shenci [1 ]
Poh, Si Bei [1 ]
Zhao, Yu [1 ]
机构：
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 41期
基金：
新加坡国家研究基金会;
关键词：
acylation; axial chirality; enantioselectivity; kinetic resolution; N-heterocyclic carbene; AXIALLY CHIRAL BIARYLS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; SECONDARY ALCOHOLS; DERIVATIVES; LIGANDS; 2-NAPHTHOLS; CONVERSION; OXIDATION; MECHANISM;
D O I：
10.1002/anie.201406192
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1'-biaryl-2,2'-diols and amino alcohols to provide them in uniformly >99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
引用
收藏
页码：11041 / 11045
页数：5
相关论文
共 84 条
  • [21] Synthesis of NOBIN derivatives for asymmetric catalysis
    Ding, KL
    Guo, HC
    Li, X
    Yuan, Y
    Wang, Y
    [J]. TOPICS IN CATALYSIS, 2005, 35 (1-2) : 105 - 116
  • [22] Iron-Catalyzed Asymmetric Aerobic Oxidation: Oxidative Coupling of 2-Naphthols
    Egami, Hiromichi
    Katsuki, Tsutomu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (17) : 6082 - +
  • [23] Fiori KW, 2009, NAT CHEM, V1, P630, DOI [10.1038/NCHEM.410, 10.1038/nchem.410]
  • [24] Nucleophilic chiral amines as catalysts in asymmetric synthesis
    France, S
    Guerin, DJ
    Miller, SJ
    Lectka, T
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2985 - 3012
  • [25] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine
    Fu, GC
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 542 - 547
  • [26] Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant
    Guo, Qi-Xiang
    Wu, Zhi-Jun
    Luo, Zhi-Bin
    Liu, Quan-Zhong
    Ye, Jian-Liang
    Luo, Shi-Wei
    Cun, Lin-Feng
    Gong, Liu-Zhu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) : 13927 - 13938
  • [27] Gustafson J.L., 2011, Angewandte Chemie, V123, P5231, DOI DOI 10.1002/ANGE.201101147
  • [28] Synthesis of Atropisomerically Defined, Highly Substituted Biaryl Scaffolds through Catalytic Enantioselective Bromination and Regioselective Cross-Coupling
    Gustafson, Jeffrey L.
    Lim, Daniel
    Barrett, Kimberly T.
    Miller, Scott J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5125 - 5129
  • [29] Dynamic Kinetic Resolution of Biaryl Atropisomers via Peptide-Catalyzed Asymmetric Bromination
    Gustafson, Jeffrey L.
    Lim, Daniel
    Miller, Scott J.
    [J]. SCIENCE, 2010, 328 (5983) : 1251 - 1255
  • [30] Mechanistic study of asymmetric oxidative biaryl coupling: Evidence for self-processing of the copper catalyst to achieve control of oxidase vs oxygenase activity
    Hewgley, J. Brian
    Stahl, Shannon S.
    Kozlowski, Marisa C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) : 12232 - +
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