Resolution-free route to chiral 2,2′-bis(pyridin-2-yl)-1,1′-binaphthyl ligand:: photochemical CpCo(CO)2-mediated cycloaddition of enantiopure 2,2′-dicyano-1,1′-binaphthyl with diynes

被引:14
|
作者
Hoshi, T
Katano, M
Nozawa, E
Suzuki, T
Hagiwara, H
机构
[1] Niigata Univ, Fac Engn, Niigata 9502181, Japan
[2] Niigata Univ, Grad Sch Sci & Technol, Niigata 9502181, Japan
关键词
D O I
10.1016/j.tetlet.2004.02.155
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A resolution-free route to chiral 2.2'-bis(pyridin-2-yl)-1.1'-binaphthyl ligands 2 was developed for the first time based on the photochemical CpCo(CO)(2)-mediated cycloaddition reaction of enantiopure 2.2'-dicyano-1.1'-binaphthyl 3 with 1.6-heptadiyne. 1,7-octadiyne, 1,8-nonadiyne, and 2.8-decadiyne. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3489 / 3491
页数:3
相关论文
共 50 条
  • [1] Practical synthetic protocols of enantiopure 1,1′-binaphthyl-2,2′-dicarboxylic acid and 2,2′-dicyano-1,1′-binaphthyl starting from optically active dibromide precursor
    Hoshi, T
    Nozawa, E
    Katano, M
    Suzuki, T
    Hagiwara, H
    TETRAHEDRON LETTERS, 2004, 45 (17) : 3485 - 3487
  • [2] INTRAMOLECULAR CYCLOADDITION OF [1,1'-BINAPHTHYL]-2,2'-BIS(ALLYLAMINE)
    NAKAMURA, Y
    ZSINDELY, J
    SCHMID, H
    HELVETICA CHIMICA ACTA, 1977, 60 (01) : 247 - 253
  • [3] 2,2′-Bis(allyloxy)-1,1′-binaphthyl
    Ge, Jia-Zhen
    Li, Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1179 - U3440
  • [4] (R)-2,2 '-Bis(methoxymethoxy)-1,1 '-binaphthyl
    Zhou, Liang
    Eli, Wumanjiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1361 - +
  • [5] (R)-(+)-2,2′-bis(diphenylphosphinoyl)1,1′-binaphthyl
    Bunten, KA
    Farrar, DH
    Lough, AJ
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2000, 56 : E267 - E267
  • [6] (S)-2,2′-bis(dicyclohexylphosphinoamino)-1,1′-binaphthyl
    Guo, RW
    Wang, LL
    Wu, J
    Choi, MCK
    Zhou, ZY
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2002, 58 : O598 - O599
  • [7] (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL AND (S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL (BINAP) - (PHOSPHINE, [1,1'-BINAPHTHALENE]-2,2'-DIYLBIS[DIPHENYLPHOSPHINO, (R)- OR (S)-)
    TAKAYA, H
    AKUTAGAWA, S
    NOYORI, R
    ORGANIC SYNTHESES, 1989, 67 : 20 - 32
  • [8] THE ULTRAVIOLET ABSORPTION SPECTRA OF 1,1'-BINAPHTHYL AND 2,2'-BINAPHTHYL
    FRAMPTON, VL
    EDWARDS, JD
    HENZE, HR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (06) : 2284 - 2285
  • [9] 2,2′-Bis(prop-2-ynyloxy)-1,1′-binaphthyl
    Zhang, Wu
    Cui, Qingxia
    Yu, Zhaowen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O317 - U5457
  • [10] (S)-(-)-2,2′-Bis(2-methylallyloxy)-1,1′-binaphthyl
    Ricken, Stefan
    Angelovski, Goran
    Schuermann, Markus
    Preut, Hans
    Eilbracht, Peter
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O551 - O552