Chiral N,N′-dioxide-In(OTf)3-catalyzed asymmetric vinylogous Mukaiyama aldol reactions

被引：19
|
作者：
Fu, Kai [1 ]
Zheng, Jianfeng [1 ]
Lin, Lili [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ,2 ]
机构：
[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 15期
基金：
中国国家自然科学基金;
关键词：
LEWIS-BASE ACTIVATION; DIELS-ALDER REACTION; ADDITION-REACTIONS; KETENE ACETALS; ALDEHYDES; KETONES; FRAGMENT; LIGANDS; ACIDS; CALLIPELTOSIDE;
D O I：
10.1039/c4cc09820j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Chiral N,N'-dioxide-In(OTf)(3) complexes were developed as efficient catalysts to catalyze the vinylogous Mukaiyama aldol reaction of the silyl dienol ester with aldehydes. The corresponding delta-hydroxy-alpha,beta-unsaturated esters were obtained in up to 99% yield and 98% ee. Moreover, the obtained (R)-3v can be easily transformed to natural bioactive products.
引用
收藏
页码：3106 / 3108
页数：3
相关论文
共 50 条
  • [41] Chiral N,N′-dioxide-FeCl3 complex-catalyzed asymmetric intramolecular Cannizzaro reaction
    Wu, Wangbin
    Liu, Xiaohua
    Zhang, Yuheng
    Ji, Jie
    Huang, Tianyu
    Lin, Lili
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2015, 51 (58) : 11646 - 11649
  • [42] Chiral N,N′-Dioxide/Scandium(III)-Catalyzed Asymmetric Alkylation of N-Unprotected 3-Substituted Oxindoles
    He, Changqiang
    Cao, Weidi
    Zhang, Jianlin
    Ge, Shulin
    Feng, Xiaoming
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (22) : 4301 - 4305
  • [43] AUXILIARY STRUCTURE AND ASYMMETRIC INDUCTION IN THE MUKAIYAMA-ALDOL REACTIONS OF CHIRAL SILYL KETENE ACETALS
    GENNARI, C
    MOLINARI, F
    COZZI, P
    OLIVA, A
    TETRAHEDRON LETTERS, 1989, 30 (38) : 5163 - 5166
  • [44] Al(OTf)3-Catalyzed Regioselective N2-Arylation of Tetrazoles with Diazo Compounds
    Zhou, Shuqi
    Li, Chunyan
    Zeng, Jie
    Lv, Jian
    Liao, Jie
    Wang, Haifeng
    Yan, Qiongjiao
    Gu, Shuangxi
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (11): : 7859 - 7864
  • [45] Asymmetric Direct Vinylogous Aldol Reaction of Furanone Derivatives Catalyzed by an Axially Chiral Guanidine Base
    Ube, Hitoshi
    Shimada, Naoki
    Terada, Masahiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (10) : 1858 - 1861
  • [46] Theoretical study on the mechanism and selectivity of asymmetric cycloaddition reactions of 3-vinylindole catalyzed by chiral N,N′-dioxide-Ni (II) complex
    Zuo, Yini
    Su, Zhishan
    Wang, Junming
    Hu, Changwei
    CATALYSIS TODAY, 2017, 298 : 130 - 137
  • [47] Enantioselective aldol reactions of trichlorosilyl enol ethers catalyzed by chiral N,N′-dioxides and monodentate N-oxides
    Nakajima, M
    Yokota, T
    Saito, M
    Hashimoto, S
    TETRAHEDRON LETTERS, 2004, 45 (01) : 61 - 64
  • [48] Support Effect on Stereoselectivities of Vinylogous Mukaiyama-Michael Reactions Catalyzed by Immobilized Chiral Copper Complexes
    Fraile, Jose M.
    Garcia, Nuria
    Herrerias, Clara I.
    ACS CATALYSIS, 2013, 3 (12): : 2710 - 2718
  • [49] Chiral N,N′-dioxide-iron(iii)-catalyzed asymmetric sulfoxidation with hydrogen peroxide
    Wang, Fang
    Feng, Lili
    Dong, Shunxi
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2020, 56 (21) : 3233 - 3236
  • [50] Chemoinformatic Catalyst Selection Methods for the Optimization of Copper-Bis(oxazoline)-Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions
    Olen, Casey L.
    Zahrt, Andrew F.
    Reilly, Sean W.
    Schultz, Danielle
    Emerson, Khateeta
    Candito, David
    Wang, Xiao
    Strotman, Neil A.
    Denmark, Scott E.
    ACS CATALYSIS, 2024, 14 (04) : 2642 - 2655
12345