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
  • [41] N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones
    Atienza, Roxanne L.
    Roth, Howard S.
    Scheidt, Karl A.
    CHEMICAL SCIENCE, 2011, 2 (09) : 1772 - 1776
  • [42] Palladium N-Heterocyclic Carbene-Catalyzed Aminations: An Outline
    S. B. Umabharathi
    Mohan Neetha
    Gopinathan Anilkumar
    Topics in Current Chemistry, 2024, 382
  • [43] N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes
    Zhang, Zhihao
    Zou, Xin
    Li, Zhenjiang
    Gao, Yu
    Qu, Yuanyuan
    Quan, Yusheng
    Zhou, Yi
    Li, Jinlan
    Sun, Jie
    Guo, Kai
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (21): : 6074 - 6079
  • [44] N-Heterocyclic carbene-catalyzed remote C(sp3)-H acylation of amides
    Xu, Huiwei
    Mo, Jia-Nan
    Liu, Wen -Deng
    Zhao, Jiannan
    TETRAHEDRON LETTERS, 2023, 121
  • [45] α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals
    Wang, Xu
    Wu, Zijun
    Wang, Jian
    ORGANIC LETTERS, 2016, 18 (03) : 576 - 579
  • [46] N-Heterocyclic Carbene-Catalyzed Oxidative Amidation of Aldehydes with Amines
    Alanthadka, Anitha
    Maheswari, C. Uma
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (06) : 1199 - 1203
  • [47] N-Heterocyclic Carbene-Catalyzed α-Alkylation of Ketones with Primary Alcohols
    Zhu, Yanfang
    Cai, Chun
    Lu, Guoping
    HELVETICA CHIMICA ACTA, 2014, 97 (12) : 1666 - 1671
  • [48] Direct and efficient N-heterocyclic carbene-catalyzed hydroxymethylation of aldehydes
    Kuhl, Nadine
    Glorius, Frank
    CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 573 - 575
  • [49] A continuing challenge: N-heterocyclic carbene-catalyzed syntheses of γ-butyrolactones
    Murauski, Kathleen J. R.
    Jaworski, Ashley A.
    Scheidt, Karl A.
    CHEMICAL SOCIETY REVIEWS, 2018, 47 (05) : 1773 - 1782
  • [50] N-Heterocyclic Carbene-Catalyzed Hydroacylation of Unactivated Double Bonds
    Hirano, Keiichi
    Biju, Akkattu T.
    Piel, Isabel
    Glorius, Frank
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (40) : 14190 - +
12345