Pd- and Mo-Catalyzed Asymmetric Allylic Alkylation

被引:190
|
作者
Trost, Barry M. [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
ENANTIOSELECTIVE TOTAL-SYNTHESIS; CONCISE SYNTHESIS; CONDURITOL B; STRATEGY; TRANSFORMATIONS; LIGANDS; AAA; CHROMANS; CENTERS; ESTERS;
D O I
10.1021/op200294r
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The ability to control the alkylation of organic substrates becomes ever more powerful by using metal catalysts. Among the major benefits of metal catalysis is the possibility to perform such processes asymmetrically using only catalytic amounts of the chiral inducing agent which is a ligand to the metal of the catalyst. A unique aspect of asymmetric metal-catalyzed processes is the fact that many mechanisms exist for stereoinduction. Furthermore, with the use of the same catalyst system, many types of bonds including but not limited to C-C, C-N, C-O, C-S, C-P, and C-H can be formed asymmetrically. An overview of this process using palladium- and molybdenum-based metals being developed in my laboratories and how it influences strategy in synthesizing bioactive molecular targets is presented.
引用
收藏
页码:185 / 194
页数:10
相关论文
共 50 条
  • [1] Designed ligands as probes for the catalytic binding mode in mo-catalyzed asymmetric allylic alkylation
    Trost, BM
    Dogra, K
    Hachiya, I
    Emura, T
    Hughes, DL
    Krska, S
    Reamer, RA
    Palucki, M
    Yasuda, N
    Reider, PJ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (11) : 1929 - +
  • [2] Synthesis of (-)-Δ9-trans-Tetrahydrocannabinol:: Stereocontrol via Mo-catalyzed asymmetric allylic alkylation reaction
    Trost, Barry M.
    Dogra, Kalindi
    ORGANIC LETTERS, 2007, 9 (05) : 861 - 863
  • [3] Pd-catalyzed asymmetric α-allylic alkylation of thioamides
    Rong, Bin
    Yang, Qin
    Liu, Yong
    Xu, Hong
    Hu, Yifan
    Cheng, Xuejing
    Zhao, Baoguo
    TETRAHEDRON LETTERS, 2015, 56 (04) : 595 - 598
  • [4] Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles
    Trost, Barry M.
    Zhang, Yong
    Journal of the American Chemical Society, 2007, 129 (47): : 14548 - 14549
  • [5] Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles
    Trost, Barry M.
    Zhang, Yong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (47) : 14548 - +
  • [6] Carbohydrate-Based Pyridine-2-carboxamides for Mo-Catalyzed Asymmetric Allylic Alkylations
    Del Litto, Raffaella
    Benessere, Vincenzo
    Ruffo, Francesco
    Moberg, Christina
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (09) : 1352 - 1356
  • [7] Pd-Catalyzed Dearomative Asymmetric Allylic Alkylation of Naphthols with Alkoxyallenes
    Hu, Jinjin
    Pan, Shulei
    Zhu, Shuai
    Yu, Peiyuan
    Xu, Ruigang
    Zhong, Guofu
    Zeng, Xiaofei
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (12): : 7896 - 7904
  • [8] Chiral pyridinyloxazolidine ligands for the Pd-catalyzed asymmetric allylic alkylation
    Yoon, JK
    Lee, SJ
    Kim, YM
    Jin, MJ
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (09) : 1239 - 1240
  • [9] Application of Walphos Ligand in the Pd(0)-Catalyzed Asymmetric Allylic Alkylation Reaction
    Marinho, Vanda R.
    Burke, Anthony J.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (24) : 4423 - 4428
  • [10] Pd-catalyzed asymmetric allylic alkylation using furanoside diphosphinite ligands
    Guimet, E
    Diéguez, M
    Ruiz, A
    Claver, C
    INORGANICA CHIMICA ACTA, 2005, 358 (13) : 3824 - 3828