Design of Bronsted acid-assisted chiral Bronsted acid catalyst bearing a bis(triflyl) methyl group for a Mannich-type reaction

被引：127
|
作者：
Hasegawa, Aiko
Naganawa, Yuki
Fushimi, Makoto
Ishihara, Kazuaki
Yamamoto, Hisashi
机构：
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
[2] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 15期
关键词：
D O I：
10.1021/ol060939a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new Bronsted acid-assisted chiral Bronsted (chiral BBA) acid catalyst (1) was developed by substituting a hydroxy group of optically active 1,1'-bi(2-naphthol) with a stronger Bronsted acidic group such as a bis(trifluoromethanesulfonyl) methyl group. The enantioselective Mannich-type reaction of ketene silyl acetals with aldimines catalyzed by (R)-1 in the presence of stoichiometric achiral proton sources gave (S)-beta-amino esters in high yield with moderate to good enantiomeric excesses.
引用
收藏
页码：3175 / 3178
页数：4
相关论文
共 50 条
  • [41] Stereoselective Mannich-type reaction of chiral aldimines with 2-silyloxybutadienes by using trifluoromethanesulfonic acid
    Ishimaru, K
    Kojima, T
    TETRAHEDRON LETTERS, 2003, 44 (29) : 5441 - 5444
  • [42] Efficient Lewis acid-assisted Bronsted acid (LBA) catalysis in the iron-catalyzed Friedel-Crafts alkylation reaction of indoles
    Jiang, Zhen-Yu
    Wu, Ji-Rong
    Li, Li
    Chen, Xi-Huai
    Lai, Guo-Qiao
    Jiang, Jian-Xiong
    Lu, Yixin
    Xu, Li-Wen
    CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2010, 8 (03): : 669 - 673
  • [43] LEWIS-ACID ASSISTED CHIRAL BRONSTED ACID FOR ENANTIOSELECTIVE PROTONATION OF SILYL ENOL ETHERS AND KETENE BIS(TRIALKYLSILYL) ACETALS
    ISHIHARA, K
    KANEEDA, M
    YAMAMOTO, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) : 11179 - 11180
  • [44] Theory-guided design of Bronsted acid-assisted phosphine catalysis: synthesis of dihydropyrones from aldehydes and allenoates
    Creech, Gardner S.
    Zhu, Xue-Feng
    Foncivic, Branden
    Dudding, Travis
    Kwon, Ohyun
    TETRAHEDRON, 2008, 64 (29) : 6935 - 6942
  • [45] Hydrogen Bonds-Enabled Design of a C1-Symmetric Chiral Bronsted Acid Catalyst
    Momiyama, Norie
    Funayama, Kosuke
    Noda, Hirofumi
    Yamanaka, Masahiro
    Akasaka, Naohiko
    Ishida, Shintaro
    Iwamoto, Takeaki
    Terada, Masahiro
    ACS CATALYSIS, 2016, 6 (02): : 949 - 956
  • [46] Enantioselective biomimetic cyclization of isoprenoids using Lewis acid-assisted chiral Bronsted acids: Abnormal Claisen rearrangements and successive cyclizations
    Nakamura, S
    Ishihara, K
    Yamamoto, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) : 8131 - 8140
  • [47] Enantioselective biomimetic cyclization of isoprenoids using Lewis acid-assisted chiral Bronsted acids: Abnormal Claisen rearrangements and successive cyclizations
    Nakamura, Shingo
    Ishihara, Kazuaki
    Yamamoto, Hisashi
    1600, ACS, Washington, DC, USA (122):
  • [48] Enantioselective Synthesis of Difluoroalkylated Isoindolinones via Chiral Spirocyclic Phosphoric Acid Catalyzed Mannich-Type Reaction
    Wang, Lei
    Zhong, Jialing
    Lin, Xufeng
    SYNLETT, 2021, 32 (04) : 417 - 422
  • [49] Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective Mannich-Type Reaction between Enamides and Thiazolones
    Kikuchi, Jun
    Momiyama, Norie
    Terada, Masahiro
    ORGANIC LETTERS, 2016, 18 (11) : 2521 - 2523
  • [50] Methyl orange dye adsorbed biochar as a potential Bronsted acid catalyst for microwave-assisted biodiesel production
    Chellappan, Suchith
    Kallingal, Aparna
    Vandana, Sajith
    Nair, Vaishakh
    Chinglenthoiba, Chingakham
    ENVIRONMENTAL SCIENCE AND POLLUTION RESEARCH, 2023, 30 (60) : 125158 - 125164
12345