Highly enantioselective Pd-catalyzed allylic alkylations of acyclic ketones

被引:114
|
作者
Yan, XX
Liang, CG
Zhang, Y
Hong, W
Cao, BX
Dai, LX
Hou, XL
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China
关键词
alkylation; enantioselectivity; enolates; ketones; palladium;
D O I
10.1002/anie.200502020
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Pocket the difference: Highly enantioselective allylic alkylation of simple acyclic ketones is carried out by using a Pd catalyst with a "chiral pocket" ligand 1 (see scheme). The addition of a Lewis acid such as AgBr and the selection of one enolate form over another dramatically affect the enantioselectivity of the reaction. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6544 / 6546
页数:3
相关论文
共 50 条
  • [1] Enantioselective Pd-Catalyzed Allylation of Acyclic α-Fluorinated Ketones
    Wang, Wengui
    Shen, Haiming
    Wan, Xiao-Long
    Chen, Qing-Yun
    Guo, Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (13): : 6347 - 6353
  • [2] Enantioselective Pd-Catalyzed Decarboxylative Allylic Alkylation of Thiopyranones. Access to Acyclic, Stereogenic α-Quaternary Ketones
    Alexy, Eric J.
    Virgil, Scott C.
    Bartberger, Michael D.
    Stoltz, Brian M.
    ORGANIC LETTERS, 2017, 19 (19) : 5007 - 5009
  • [3] Highly stereoselective peptide modifications through Pd-catalyzed allylic alkylations of chelated peptide enolates
    Deska, Jan
    Kazmaier, Uli
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (21) : 6204 - 6211
  • [4] New ligands for regio- and enantiocontrol in Pd-catalyzed allylic alkylations
    Prétôt, R
    Pfaltz, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (03) : 323 - 325
  • [5] Highly regio-, diastereo-, and enantioselective Pd-catalyzed allylic alkylation of acyclic ketone enolates with monosubstituted allyl substrates
    Zheng, Wen-Hua
    Zheng, Bao-Hui
    Zhang, Yan
    Hou, Xue-Long
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) : 7718 - +
  • [6] Synthesis of γ-Lactams and γ-Lactones via Intramolecular Pd-Catalyzed Allylic Alkylations
    Kammerer, Claire
    Prestat, Guillaume
    Madec, David
    Poli, Giovanni
    ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) : 3439 - 3447
  • [7] Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates
    Trost, BM
    Xu, JY
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2846 - 2847
  • [8] Regio- and enantioselective Pd-catalyzed allylic alkylation of ketones through allyl enol carbonates
    1600, American Chemical Society, Columbus, United States (127):
  • [9] Pd-catalyzed highly regio-, diastereo-, and enantioselective allylic alkylation of α-fluorophosphonates
    Huang, Ying
    Zhang, Qing-Song
    Fang, Ping
    Chen, Tie-Gen
    Zhu, Jun
    Hou, Xue-Long
    CHEMICAL COMMUNICATIONS, 2014, 50 (51) : 6751 - 6753
  • [10] Highly enantioselective Pd-catalyzed allylic alkylation using new chiral ferrocenylphosphinoimidazolidine ligands
    Jin, MJ
    Takale, VB
    Sarkar, MS
    Kim, YM
    CHEMICAL COMMUNICATIONS, 2006, (06) : 663 - 664