Regioselective alkylation of lithium dienediolates of α,β-unsaturated carboxylic acids

被引：0
作者：
Brun, EM [1 ]
Gil, S [1 ]
Mestres, R [1 ]
Parra, M [1 ]
机构：
[1] Univ Valencia, Dept Quim Organ, Valencia, Spain
来源：
SYNTHESIS-STUTTGART | 2000年 / 08期
关键词：
lithium enolates; alkylation; alkyl sulfonates; carboxylic acids; diastereoselectivity;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Lithium carboxylic acids dienediolates are regioselectively alkylated at the a-carbon by reaction with tosylates derived from both primary and secondary alcohols. Both regio- and diastereoselectivity are improved when compared with those obtained in the corresponding alkylation with alkyl halides.
引用
收藏
页码：1160 / 1165
页数：6
相关论文
共 50 条
  • [21] Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates.: A comparative study with lithium enolates
    Quesnel, Y
    Bidois-Sery, L
    Poirier, JM
    Duhamel, L
    SYNLETT, 1998, (04) : 413 - +
  • [22] Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions
    Liu, Weiping
    Sahoo, Basudev
    Spannenberg, Anke
    Junge, Kathrin
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (36) : 11673 - 11677
  • [23] LiClO4-activated stereo- and regioselective alkylation of aldehydes
    Markert, M
    Buchem, I
    Krüger, H
    Mahrwald, R
    TETRAHEDRON, 2004, 60 (04) : 993 - 999
  • [24] Rhodium(I)-Catalyzed C2-Selective Decarbonylative C-H Alkylation of Indoles with Alkyl Carboxylic Acids and Anhydrides
    Yu, Haiyang
    Zhao, Haoqiang
    Xu, Xin
    Zhang, Xin
    Yu, Zexin
    Li, Lingchao
    Wang, Peng
    Shi, Qian
    Xu, Lijin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 879 - 885
  • [25] Photocatalyst-free visible light induced decarboxylative alkylation of quinoxalin-2(1H)-ones with carboxylic acids
    Hong, Yun-Yun
    Peng, Zhen
    Ma, Hui
    Zhu, Qi
    Xu, Xiang-Qin
    Yang, Li-Hua
    Xie, Long-Yong
    TETRAHEDRON LETTERS, 2022, 89
  • [26] Selective Synthesis of 1-O-Alkyl(poly)glycerol Ethers by Catalytic Reductive Alkylation of Carboxylic Acids with a Recyclable Catalytic System
    Sutter, Marc
    Dayoub, Wissam
    Metay, Estelle
    Raoul, Yann
    Lemaire, Marc
    CHEMSUSCHEM, 2012, 5 (12) : 2397 - 2409
  • [27] Copper-Catalyzed Di- and Trifluoromethylation of α,β-Unsaturated Carboxylic Acids: A Protocol for Vinylic Fluoroalkylations
    He, Zhengbiao
    Luo, Tao
    Hu, Mingyou
    Cao, Yanjing
    Hu, Jinbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) : 3944 - 3947
  • [28] Metal-Free Decarboxylative Cyanomethylation of β-Aryl/Heteroaryl Substituted α,β-Unsaturated Carboxylic Acids to γ-Ketonitriles
    Chand, Shiv
    Kumar, Saurabh
    Sharma, Anup Kumar
    Singh, Krishna Nand
    ORGANIC LETTERS, 2024, 26 (46) : 10051 - 10055
  • [29] Pd-Catalyzed decarboxylative cross-coupling reactions of epoxides with α,β-unsaturated carboxylic acids
    Lu, Xiao-Yu
    Li, Jin-Song
    Wang, Shi-Qun
    Zhu, Yu-Jing
    Li, Yue-Ming
    Yan, Lu-Yu
    Li, Jia-Mei
    Wang, Jin-Yu
    Zhou, Hai-Pin
    Ge, Xiu-Tao
    CHEMICAL COMMUNICATIONS, 2019, 55 (74) : 11123 - 11126
  • [30] Visible Light-Induced Decarboxylative Alkylation of Heterocyclic Aromatics with Carboxylic Acids via Anthocyanin as a Photocatalyst
    Guo, Rui
    Zuo, Minghui
    Tian, Qinye
    Hou, Chuanfu
    Sun, Shouneng
    Guo, Weihao
    Wu, Hongfeng
    Chu, Wenyi
    Sun, Zhizhong
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (13) : 1976 - 1981
12345