Iridium/Chiral Diene-Catalyzed Enantioselective (3+2) Annulation of Aromatic Ketimines with 1,3-Enynes via C-H Activation

被引:40
作者
Nagamoto, Midori [1 ]
Sakamoto, Kana [2 ]
Nishimura, Takahiro [2 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
[2] Osaka City Univ, Dept Chem, Grad Sch Sci, Osaka 5588585, Japan
关键词
Iridium; C-H activation; enynes; annulation; chiral dienes; N-SULFONYL KETIMINES; BOND ACTIVATION; INDENE FRAMEWORKS; ACYL KETIMINES; ALKYNES; LIGANDS; FUNCTIONALIZATION; 1,3-DIENES; COMPLEXES; KETONES;
D O I
10.1002/adsc.201701378
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An iridium/chiral diene complex efficiently catalyzed enantioselective (3+2) annulation between 1,3-enynes and cyclic N-acyl ketimines generated insitu from 3-aryl-3-hydroxyisoindoin-1-ones. The reaction gave the corresponding aminoindane derivatives in high yields with high regio-, diastereo-, and enantioselectivity.
引用
收藏
页码:791 / 795
页数:5
相关论文
共 66 条
[21]  
Hatano M., 2015, ANGEW CHEM, V127, P11099, DOI [10.1002/ange.201505382, DOI 10.1002/ANGE.201505382]
[22]   Hydroxoiridium/Chiral Diene Complexes as Effective Catalysts for Asymmetric Annulation of α-Oxo- and Iminocarboxamides with 1,3-Dienes [J].
Hatano, Miyuki ;
Nishimura, Takahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) :10949-10952
[23]   Transition metal-catalyzed ketone-directed or mediated C-H functionalization [J].
Huang, Zhongxing ;
Lim, Hee Nam ;
Mo, Fanyang ;
Young, Michael C. ;
Dong, Guangbin .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (21) :7764-7786
[24]   Ruthenium(II)-Catalyzed C-H Bond Activation: An Efficient Route toward Indenamines [J].
Hung, Chen-Hsun ;
Gandeepan, Parthasarathy ;
Cheng, Chien-Hong .
CHEMCATCHEM, 2014, 6 (09) :2692-2697
[25]   Rhenium- and aniline-catalyzed one-pot annulation of aromatic ketones and α,β-unsaturated esters initiated by C-H bond activation [J].
Kuninobu, Y ;
Nishina, Y ;
Shoitho, M ;
Takai, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (17) :2766-2768
[26]   Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation: Synthesis of phthalimidine and indene derivatives [J].
Kuninobu, Y ;
Tokunaga, Y ;
Kawata, A ;
Takai, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :202-209
[27]   Rhenium-catalyzed formation of indene frameworks via C-H bond activation: [3+2] annulation of aromatic aldimines and acetylenes [J].
Kuninobu, Y ;
Kawata, A ;
Takai, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13498-13499
[28]   Rhenium-Catalyzed Diastereoselective Synthesis of Aminoindanes via the Insertion of Allenes into a C-H Bond [J].
Kuninobu, Yoichiro ;
Yu, Peng ;
Takai, Kazuhiko .
ORGANIC LETTERS, 2010, 12 (19) :4274-4276
[29]   CATALYTIC C-C BOND FORMATION VIA ORTHO-METALATED COMPLEXES [J].
LEWIS, LN ;
SMITH, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) :2728-2735
[30]  
Li B.J., 2012, ANGEW CHEM, V124, P4014, DOI DOI 10.1002/ANGE.201200271