Catalytic imine-imine cross-coupling reactions

被引:48
作者
Matsumoto, Masatoshi [1 ]
Harada, Masashi [1 ]
Yamashita, Yasuhiro [1 ]
Kobayashi, Shu [1 ]
机构
[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
基金
日本学术振兴会;
关键词
POTENTIAL CHIRAL SUPERBASES; LOW-VALENT TITANIUM; CHLORIDE-INDUCED CYCLIZATION; IN-SITU GENERATION; MODIFIED GUANIDINES; AROMATIC-ALDEHYDES; VICINAL DIAMINES; GLYCINE ESTERS; DERIVATIVES; ALDIMINES;
D O I
10.1039/c4cc06156j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report here efficient catalytic imine-imine cross-coupling reactions based on an umpolung strategy; an imine bearing a 9-fluorenyl moiety on its nitrogen atom, which acted as a nucleophile, reacted with another imine to afford an imine-imine cross-coupling adduct in high yield. Furthermore, a chiral guanidine acted as a chiral catalyst for these coupling reactions, and optically active 1,2-diamines were obtained in high yields with high enantioselectivities.
引用
收藏
页码:13041 / 13044
页数:4
相关论文
共 38 条
  • [21] ACIDITIES OF GLYCINE SCHIFF-BASES AND ALKYLATION OF THEIR CONJUGATE BASES
    ODONNELL, MJ
    BENNETT, WD
    BRUDER, WA
    JACOBSEN, WN
    KNUTH, K
    LECLEF, B
    POLT, RL
    BORDWELL, FG
    MROZACK, SR
    CRIPE, TA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) : 8520 - 8525
  • [22] McMurry coupling of aryl aldehydes and imino pinacol coupling mediated by Ti(O-i-Pr)4/Me3SiCl/Mg reagent
    Okamoto, Sentaro
    He, Jing-Qian
    Ohno, Chihaya
    Oh-iwa, Yuhji
    Kawaguchi, Yuhki
    [J]. TETRAHEDRON LETTERS, 2010, 51 (02) : 387 - 390
  • [23] Direct-Type Aldol Reactions of Fluorenylidene-Protected/Activated Glycine Esters with Aldehydes for the Synthesis of ß-Hydroxy-a-amino Acid Derivatives
    Rahmani, Raphael
    Matsumoto, Masatoshi
    Yamashita, Yasuhiro
    Kobayashi, Shu
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (06) : 1191 - 1194
  • [24] New reagent for reductive coupling of carbonyl and imine compounds: Highly reactive manganese-mediated pinacol coupling of aryl aldehydes, aryl ketones, and aldimines
    Rieke, RD
    Kim, SH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) : 5235 - 5239
  • [25] Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature
    Seayad, Abdul Majeed
    Ramalingam, Balamurugan
    Yoshinaga, Kazuhiko
    Nagata, Takushi
    Chai, Christina L. L.
    [J]. ORGANIC LETTERS, 2010, 12 (02) : 264 - 267
  • [26] METHODS OF REACTIVITY UMPOLUNG
    SEEBACH, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (04): : 239 - 258
  • [27] Highly chemoselective crossed imino pinacol coupling reaction using the synergetic effect of boron trifluoride etherate and trichloromethylsilane
    Shimizu, M
    Suzuki, I
    Makino, H
    [J]. SYNLETT, 2003, (11) : 1635 - 1638
  • [28] N-Alkylation-coupling reaction of imines promoted by alkylaluminum reagents, leading to a facile synthesis of 1,2-diamines
    Shimizu, M
    Niwa, Y
    [J]. TETRAHEDRON LETTERS, 2001, 42 (15) : 2829 - 2832
  • [29] Homocoupling of aldimines mediated by zirconocene: synthesis of vicinal diamines and imidazolidines
    Soueidan, Mohamad
    Helion, Florence
    Namy, Jean-Louis
    Szymoniak, Jan
    [J]. TETRAHEDRON LETTERS, 2011, 52 (12) : 1348 - 1350
  • [30] REDUCTION AND COUPLING REACTION OF IMINES PROMOTED BY YTTERBIUM METAL
    TAKAKI, K
    TSUBAKI, Y
    TANAKA, S
    BEPPU, F
    FUJIWARA, Y
    [J]. CHEMISTRY LETTERS, 1990, (02) : 203 - 204