Kinetic Resolution of α-Hydroxyamide via N-Heterocyclic Carbene-Catalyzed Acylation

被引：9
|
作者：
Yamada, Ken-ichi [1 ,2 ]
Yamauchi, Akiho [1 ]
Fujiwara, Tatsuya [1 ]
Hashimoto, Keiji [1 ]
Wang, Yinli [1 ,3 ]
Kuwano, Satoru [3 ]
Inokuma, Tsubasa [1 ,2 ]
机构：
[1] Tokushima Univ, Grad Sch Pharmaceut Sci, Shomachi, Tokushima 7708505, Japan
[2] Tokushima Univ, Res Cluster Innovat Chem Sensing, Shomachi, Tokushima 7708505, Japan
[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 10期
关键词：
acylation; alpha-hydroxyamide; catalytic kinetic resolution; N-heterocyclic carbene; organocatalysis; CARBOXYLIC-ACIDS; AMINO-ALCOHOLS; LEAVING GROUP; DERIVATIVES; CYCLIZATION; CONVERSION;
D O I：
10.1002/ajoc.202200452
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The effect of N-substituent of alpha-hydroxyamides on the performance of chiral N-heterocyclic carbene-catalyzed kinetic resolution was examined. N-tert-Butyl-alpha-hydroxyamides provided the best performance and underwent enantioselective acylation with alpha-bromo aldehyde by chiral N-heterocyclic carbene/carboxylate anion co-catalysis to realize kinetic resolution in high selectivity factor up to 128.
引用
收藏
页数：4
相关论文
共 50 条
  • [21] N-Heterocyclic carbene-catalyzed synthesis of acetyltributylcitrate via a transesterification reaction
    Lin He
    Hao Guo
    Xiao-Wei Ma
    Jie Zhang
    Cheng-Zhi Gu
    Wei Wang
    Bin Dai
    ChineseChemicalLetters, 2014, 25 (02) : 215 - 217
  • [22] N-Heterocyclic Carbene Catalyzed Dynamic Kinetic Resolution of Pyranones
    Zhao, Changgui
    Li, Fangyi
    Wang, Jian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (05) : 1820 - U493
  • [23] N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN
    Fan, Ye-Cheng
    Du, Guang-Fen
    Sun, Wan-Fu
    Kang, Wei
    He, Lin
    TETRAHEDRON LETTERS, 2012, 53 (17) : 2231 - 2233
  • [24] N-Heterocyclic Carbene-Catalyzed β-Indolylation of α-Bromoenals with Indoles
    Sun, Shaofa
    Lang, Ming
    Wang, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (24) : 5704 - 5708
  • [25] Enantioselective N-heterocyclic carbene-catalyzed synthesis of indenopyrones
    Chen, Kun-Quan
    Zhang, Han-Ming
    Wang, Dong-Ling
    Sun, De-Qun
    Ye, Song
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) : 6694 - 6697
  • [26] N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
    Gelat, Fabien
    Patra, Atanu
    Pannecoucke, Xavier
    Biju, Akkattu T.
    Poisson, Thomas
    Besset, Tatiana
    ORGANIC LETTERS, 2018, 20 (13) : 3897 - 3901
  • [27] Palladium N-Heterocyclic Carbene-Catalyzed Aminations: An Outline
    Umabharathi, S. B.
    Neetha, Mohan
    Anilkumar, Gopinathan
    TOPICS IN CURRENT CHEMISTRY, 2024, 382 (01)
  • [28] N-Heterocyclic Carbene-Catalyzed Conjugate Additions of Alcohols
    Phillips, Eric M.
    Riedrich, Matthias
    Scheidt, Karl A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13179 - 13181
  • [29] N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides
    Xia Dengpeng
    Luo Jinvun
    He Lin
    Cai Zhihua
    Du Guangfen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (02) : 622 - 630
  • [30] Atroposelective Dynamic Kinetic Resolution via In Situ Hemiaminals Catalyzed by N-Heterocyclic Carbene
    Guo, Donghui
    Peng, Qiupeng
    Zhang, Bei
    Wang, Jian
    ORGANIC LETTERS, 2021, 23 (20) : 7765 - 7770
12345