Enantioselective Pd-catalyzed allylic alkylation of Indoles by a new class of chiral ferrocenyl P/S Ligands

被引:119
作者
Cheung, Hong Yee [1 ]
Yu, Wing-Yiu [1 ]
Lam, Fuk Loi [1 ]
Au-Yeung, Terry T. -L. [1 ]
Zhou, Zhongyuan [1 ]
Chan, Tak Hang [1 ]
Chan, Albert S. C. [1 ]
机构
[1] Hong Kong Polytech Univ, Inst Mol Technol Drug Discovery & Synthes, Open Lab Chirotechnol, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1021/ol7018532
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral ferrocenyl heterobidentate P/S ligands bearing both central and planar chirality were prepared from (S)-Ugi's amine via a three-step modular synthesis. Through systematic screening and optimization, L8 was found to be the best ligand for Pd-catalyzed asymmetric allylic alkylation of indoles with ee's up to 96% being attained.
引用
收藏
页码:4295 / 4298
页数:4
相关论文
共 25 条
  • [21] Pfaltz A., 1999, COMPREHENSIVE ASYMME, P833, DOI DOI 10.1021/CR0683515
  • [22] 1-Phosphino-2-sulfenylferrocenes:: efficient ligands in enantioselective palladium-catalyzed allylic substitutions and ring opening of 7-oxabenzonorbornadienes
    Priego, J
    Mancheño, OG
    Cabrera, S
    Arrayás, RG
    Llamas, T
    Carretero, JC
    [J]. CHEMICAL COMMUNICATIONS, 2002, (21) : 2512 - 2513
  • [23] Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis
    Trost, BM
    Crawley, ML
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2921 - 2943
  • [24] Catalytic enantioselective Friedel-Crafts/Michael addition reactions of indoles to ethenetricarboxylates
    Yamazaki, S
    Iwata, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02) : 739 - 743
  • [25] Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C3-symmetric trisoxazoline copper(II) complexes
    Zhou, J
    Ye, MC
    Huang, ZZ
    Tang, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) : 1309 - 1320