Catalytic imine-imine cross-coupling reactions

被引:49
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 [J].
ODONNELL, MJ ;
BENNETT, WD ;
BRUDER, WA ;
JACOBSEN, WN ;
KNUTH, K ;
LECLEF, B ;
POLT, RL ;
BORDWELL, FG ;
MROZACK, SR ;
CRIPE, TA .
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 [J].
Okamoto, Sentaro ;
He, Jing-Qian ;
Ohno, Chihaya ;
Oh-iwa, Yuhji ;
Kawaguchi, Yuhki .
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 [J].
Rahmani, Raphael ;
Matsumoto, Masatoshi ;
Yamashita, Yasuhiro ;
Kobayashi, Shu .
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 [J].
Rieke, RD ;
Kim, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15) :5235-5239
[25]   Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature [J].
Seayad, Abdul Majeed ;
Ramalingam, Balamurugan ;
Yoshinaga, Kazuhiko ;
Nagata, Takushi ;
Chai, Christina L. L. .
ORGANIC LETTERS, 2010, 12 (02) :264-267
[26]   METHODS OF REACTIVITY UMPOLUNG [J].
SEEBACH, D .
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 [J].
Shimizu, M ;
Suzuki, I ;
Makino, H .
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 [J].
Shimizu, M ;
Niwa, Y .
TETRAHEDRON LETTERS, 2001, 42 (15) :2829-2832
[29]   Homocoupling of aldimines mediated by zirconocene: synthesis of vicinal diamines and imidazolidines [J].
Soueidan, Mohamad ;
Helion, Florence ;
Namy, Jean-Louis ;
Szymoniak, Jan .
TETRAHEDRON LETTERS, 2011, 52 (12) :1348-1350
[30]   REDUCTION AND COUPLING REACTION OF IMINES PROMOTED BY YTTERBIUM METAL [J].
TAKAKI, K ;
TSUBAKI, Y ;
TANAKA, S ;
BEPPU, F ;
FUJIWARA, Y .
CHEMISTRY LETTERS, 1990, (02) :203-204