Chiral Phosphoric Acid-Catalyzed Asymmetric Friedel-Crafts Addition of Indolizine to Cyclic N-Sulfonyl Imine

被引：6
|
作者：
Subba, Parbat [1 ]
Sadhu, Milon M. [1 ]
Singh, Vinod K. [1 ]
机构：
[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 20期
关键词：
CONJUGATE ADDITION; FLUOROPHORE; SCAFFOLDS; DISCOVERY; ACCESS;
D O I：
10.1021/acs.joc.3c01686
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient chiral phosphoric acid-catalyzed enantioselective Friedel-Crafts addition of indolizine to cyclic N-sulfonyl imine has been established. The newly developed protocol, which probably proceeds via a monoactivation reaction pathway, allows the access of enantioenriched sulfonamide functionalized indolizines with excellent yields (up to 99%) and enantioselectivities (up to 99%). Moreover, the synthetic utility of this protocol has been explored with some chemical transformations.
引用
收藏
页码：14676 / 14687
页数：12
相关论文
共 50 条
  • [21] Enantioselective Friedel-Crafts Alkylation of Indoles, Pyrroles, and Furans with Trifluoropyruvate Catalyzed by Chiral Phosphoric Acid
    Kashikura, Wataru
    Itoh, Junji
    Mori, Keiji
    Akiyama, Takahiko
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (03) : 470 - 472
  • [22] Synthesis of six-membered spirooxindoles via a chiral Bronsted acid-catalyzed asymmetric intramolecular Friedel-Crafts reaction
    Chen, Hui-Xuan
    Zhang, Yaqi
    Zhang, Yuyang
    He, Xuefeng
    Zhang, Zhen-Wei
    Liang, Hao
    He, Wenhuan
    Jiang, Xiaoding
    Chen, Xiangmeng
    Qiu, Liqin
    RSC ADVANCES, 2018, 8 (65): : 37035 - 37039
  • [23] Hydrobromic acid-catalyzed Friedel-Crafts type reactions of naphthols
    Xu, Cong
    Yuan, Hongjuan
    Liu, Yingjie
    Wang, Mang
    Liu, Qun
    RSC ADVANCES, 2014, 4 (04): : 1559 - 1562
  • [24] Lewis acid-catalyzed Friedel-Crafts alkylation of ferrocene with allylchlorosilanes
    Ahn, S
    Song, YS
    Yoo, BR
    Jung, IN
    ORGANOMETALLICS, 2000, 19 (14) : 2777 - 2780
  • [25] Chiral Bronsted acid catalyzed Friedel-Crafts alkylation reactions
    You, Shu-Li
    Cai, Quan
    Zeng, Mi
    CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2190 - 2201
  • [26] Friedel-Crafts Reaction of Indoles with N-Sulfonyl Imines Catalyzed by H3PW12O40
    Hui, Yonghai
    Wang, Changchun
    Shi, Wei
    Meng, Hua
    Xie, Zhengfeng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (05) : 898 - 902
  • [27] Enantioselective Synthesis of Fluorene Derivatives by Chiral Phosphoric Acid Catalyzed Tandem Double Friedel-Crafts Reaction
    Sun, Feng-Lai
    Zeng, Mi
    Gu, Qing
    You, Shu-Li
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (35) : 8709 - 8712
  • [28] Enantioselective Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid
    Bachu, Prabhakar
    Akiyama, Takahiko
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4112 - 4114
  • [29] Chiral Bronsted Acid-Catalyzed Intramolecular Asymmetric Dearomatization Reaction of Indoles with Cyclobutanones via Cascade Friedel-Crafts/Semipinacol Rearrangement
    Yu, Xuan
    Zheng, Chao
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (37) : 25878 - 25887
  • [30] Asymmetric Organocatalytic Aza-Friedel-Crafts Reaction of Naphthols with N-Sulfonyl Imines
    Chauhan, Pankaj
    Chimni, Swapandeep Singh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (09) : 1636 - 1640
12345