Regio- and enantioselective carbolithiation of non-activated C=C bonds

被引：22
|
作者：
Norsikian, S [1 ]
Baudry, M [1 ]
Normant, JF [1 ]
机构：
[1] Univ Paris 06, Associe CNRS, Lab Chim Organo Elements, F-75252 Paris 05, France
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 34期
关键词：
carbometalation; (-)-sparteine; enantioselection;
D O I：
10.1016/S0040-4039(00)01091-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Primary alkyllithiums in the presence of (-)-sparteine, add to terminal conjugated dienes. They also add to 2,4-pentadien-1-ols if they are substituted on C(5), and give rise to allyllithium intermediates, 2-Alkylalkan-1-ols have thus been prepared with ee's up to 74%. (C) 2000 Elsevier Science Ltd, All rights reserved.
引用
收藏
页码：6575 / 6578
页数：4
相关论文
共 50 条
  • [31] A nucleobase- driven P450 peroxidase system enables regio- and stereo- specific formation of C―C and C―N bonds
    Wei, Guangzheng
    Duan, Borui
    Zhou, Tai-Ping
    Tian, Wenya
    Sun, Chenghai
    Lin, Zhi
    Deng, Zixin
    Wang, Binju
    Zhang, Zhengyu
    Qu, Xudong
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2024, 121 (46)
  • [32] Enantioselective C(sp3)–C(sp3) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis
    Srikrishna Bera
    Runze Mao
    Xile Hu
    Nature Chemistry, 2021, 13 : 270 - 277
  • [33] Enantioselective C(sp3)-C(sp3) cross-coupling of non-activated alkyl electrophiles via nickel hydride catalysis
    Bera, Srikrishna
    Mao, Runze
    Hu, Xile
    NATURE CHEMISTRY, 2021, 13 (03) : 270 - +
  • [34] Electrophilic Activation of S-Si Reagents by Silylium Ions for Their Regio- and Diastereoselective Addition Across C-C Multiple Bonds
    Zuo, Honghua
    Irran, Elisabeth
    Klare, Hendrik F. T.
    Oestreich, Martin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (15)
  • [35] Functionalization of Non-activated C?H Bonds of Alkanes: An Effective and Recyclable Catalytic System Based on Fluorinated Silver Catalysts and Solvents
    Angeles Fuentes, M.
    Munoz, Bianca K.
    Jacob, Kane
    Vendier, Laure
    Caballero, Ana
    Etienne, Michel
    Perez, Pedro J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (04) : 1327 - 1334
  • [36] Functionalization of non-activated C-H bonds in ketones and imines with HF/SbF5/CCl4
    Thibaudeau, S
    Martin-Mingot, A
    Jouannetaud, MP
    Jacquesy, JC
    TETRAHEDRON, 2002, 58 (33) : 6643 - 6649
  • [37] Silver-Catalyzed Regio- and Stereoselective Formal Carbene Insertion into Unstrained C-C σ-Bonds of 1,3-Dicarbonyls
    Liu, Zhaohong
    Zhang, Xinyu
    Virelli, Matteo
    Zanoni, Giuseppe
    Anderson, Edward A.
    Bi, Xihe
    ISCIENCE, 2018, 8 : 54 - +
  • [38] ADDITION OF ORGANOMAGNESIUM COMPOUNDS TO NON-ACTIVATED C=C DOUBLE-BONDS .5. INTRAMOLECULAR CYCLIZATION OF 4-ALKENYLMAGNESIUM HALIDES TO CYCLOBUTYL DERIVATIVES
    LEHMKUHL, H
    REINEHR, D
    HENNEBER.D
    SCHROTH, G
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1973, 57 (01) : 49 - 53
  • [39] Metal Alkoxide Promoted Regio- and Stereoselective C=O and C=C Metathesis of Allenoates with Aldehydes
    Wang, Minyan
    Fang, Zhao
    Fu, Chunling
    Ma, Shengming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (12) : 3214 - 3217
  • [40] Asymmetric hydroamination of non-activated carbon-carbon multiple bonds
    Aillaud, Isabelle
    Collin, Jacqueline
    Hannedouche, Jerome
    Schulz, Emmanuelle
    DALTON TRANSACTIONS, 2007, (44) : 5105 - 5118
12345