Catalytic Enantioselective Protonation/Nucleophilic Addition of Diazoesters with Chiral Oxazaborolidinium Ion Activated Carboxylic Acids

被引：20
作者：
Kang, Ki-Tae [1 ,2 ]
Kim, Seung Tae [2 ]
Hwang, Geum-Sook [1 ]
Ryu, Do Hyun [2 ]
机构：
[1] Western Seoul Ctr, Korea Basic Sci Inst, 150,Bugahyeon ro, Seoul 03759, South Korea
[2] Sungkyunkwan Univ, Dept Chem, 300,Cheoncheon, Suwon 16419, South Korea
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 14期
基金：
新加坡国家研究基金会;
关键词：
asymmetric catalysis; boron; Bronsted acid; diazo compounds; reaction mechanisms; ASYMMETRIC ROSKAMP REACTION; H INSERTION REACTIONS; TROPIC ACID; KINETIC RESOLUTION; ETHYL-ESTER; PROTONATION; BOND; DERIVATIVES; CYCLOADDITIONS; MIGRATION;
D O I：
10.1002/anie.201612655
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new chiral Bronsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids.
引用
收藏
页码：3977 / 3981
页数：5
相关论文
共 50 条
  • [41] A new class of C2 chiral photodimer ligands for catalytic enantioselective diethylzinc addition to arylaldehydes
    Ueda, Yuki
    Yagishita, Fumitoshi
    Ishikawa, Hiroki
    Kaji, Yuki
    Baba, Nozomi
    Kasashima, Yoshio
    Mino, Takashi
    Sakamoto, Masami
    TETRAHEDRON, 2015, 71 (36) : 6254 - 6258
  • [42] Chiral Monodentate Phosphines and Bulky Carboxylic Acids: Cooperative Effects in Palladium-Catalyzed Enantioselective C(sp3)-H Functionalization
    Saget, Tanguy
    Lemouzy, Sebastien J.
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (09) : 2238 - 2242
  • [43] Catalytic Enantioselective Synthesis of 4-Amino-1,2,3,4-tetrahydropyridine Derivatives from Intramolecular Nucleophilic Addition Reaction of Tertiary Enamides
    Tong, Shuo
    Wang, Mei-Xiang
    SYNLETT, 2019, 30 (04) : 483 - 487
  • [44] Catalytic Regio- and Enantioselective [4+2] Annulation Reactions of Non-activated Allenes by a Chiral Cationic Indium Complex
    Wang, Le
    Lv, Jian
    Zhang, Long
    Luo, Sanzhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (36) : 10867 - 10871
  • [45] Simple derivatives of natural amino acids as chiral ligands in the catalytic asymmetric addition of phenylacetylene to aldehydes
    Han, ZJ
    Wang, R
    Zhou, YF
    Liu, L
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (05) : 934 - 938
  • [46] Atroposelective Construction of Axially Chiral Alkene-Indole Scaffolds via Catalytic Enantioselective Addition Reaction of 3-Alkynyl-2-indolylmethanols†
    Wang, Jing-Yi
    Sun, Meng
    Yu, Xian-Yang
    Zhang, Yu-Chen
    Tan, Wei
    Shi, Feng
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (08) : 2163 - 2171
  • [47] Rh-catalyzed enantioselective conjugate addition of arylboronic acids with a dynamic library of chiral tropos phosphorus ligands
    Monti, Chiara
    Gennari, Cesare
    Piarulli, Umberto
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) : 1547 - 1558
  • [48] Synergistic Chiral Ion Pair Catalysts for Asymmetric Catalytic Synthesis of Quaternary α,β-Diamino Acids
    Shi, Shi-Hui
    Huang, Fu-Ping
    Zhu, Ping
    Dong, Zhen-Wen
    Hui, Xin-Ping
    ORGANIC LETTERS, 2012, 14 (08) : 2010 - 2013
  • [49] An efficient method for catalytic enantioselective addition of diethylzinc to aryl aldehydes by a C2-symmetric chiral imino alcohol
    Salehi, Peyman
    Dabiri, Minoo
    Kozehgary, Gholamreza
    Baghbanzadeh, Mostafa
    TETRAHEDRON-ASYMMETRY, 2009, 20 (22) : 2609 - 2611
  • [50] Novel chiral pyridine N-oxide ligands and their application in the enantioselective catalytic reduction of ketones and the addition of diethylzinc to aldehydes
    Derdau, V
    Laschat, S
    Hupe, E
    König, WA
    Dix, I
    Jones, PG
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 1999, (06) : 1001 - 1007
12345