Rhodium/chiral diene-catalyzed asymmetric methylation of N-sulfonylarylimines with trimethylboroxine

被引：11
|
作者：
Nishimura, Takahiro [1 ]
Ashouri, Akram [1 ]
Ebe, Yusuke [1 ]
Maeda, Yuko [1 ]
Hayashi, Tamio [1 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
来源：
TETRAHEDRON-ASYMMETRY | 2012年 / 23卷 / 09期
关键词：
ENANTIOSELECTIVE ADDITION; DIORGANOZINC REAGENTS; DIALKYLZINC REAGENTS; ARYLBORONIC ACIDS; STEERING LIGANDS; ORGANOMETALLIC REAGENTS; ORGANOBORON REAGENTS; CHIRAL OLEFINS; 1,4-ADDITION; IMINES;
D O I：
10.1016/j.tetasy.2012.04.021
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A hydroxorhodium complex coordinated with a chiral diene ligand catalyzed the asymmetric addition of trimethylboroxine to N-sulfonylarylimines to give high yields of chiral 1-aryl-1-ethylamines with high enantioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：655 / 658
页数：4
相关论文
共 50 条
  • [1] Rhodium/Chiral Diene-Catalyzed Asymmetric Cyclopolymerization of Achiral 1,8-Diynes
    Ichikawa, Yoshitaka
    Nishimura, Takahiro
    Hayashi, Tamio
    ORGANOMETALLICS, 2011, 30 (08) : 2342 - 2348
  • [2] Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates
    Soergel, Sebastian
    Tokunaga, Norihito
    Sasaki, Keigo
    Okamoto, Kazuhiro
    Hayashi, Tamio
    ORGANIC LETTERS, 2008, 10 (04) : 589 - 592
  • [3] Synthesis of chiral cyclobutanes via rhodium/diene-catalyzed asymmetric 1,4-addition: a dramatic ligand effect on the diastereoselectivity
    Chen, Ya-Jing
    Hu, Tian-Jiao
    Feng, Chen-Guo
    Lin, Guo-Qiang
    CHEMICAL COMMUNICATIONS, 2015, 51 (42) : 8773 - 8776
  • [4] Rhodium/Chiral Diene-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to Chromones: A Highly Enantioselective Pathway for Accessing Chiral Flavanones
    He, Qijie
    So, Chau Ming
    Bian, Zhaoxiang
    Hayashi, Tamio
    Wang, Jun
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (03) : 540 - 543
  • [5] Rhodium(I)/Diene-Catalyzed Addition Reactions of Arylborons with Ketones
    Liao, Yuan-Xi
    Xing, Chun-Hui
    Hu, Qiao-Sheng
    ORGANIC LETTERS, 2012, 14 (06) : 1544 - 1547
  • [6] Rhodium(I)/Chiral Diene-Catalyzed Enantioselective Addition of Boronic Acids to N-Unsubstituted Isatin-Derived Ketimines
    Yonesaki, Ryohei
    Kusagawa, Ibuki
    Morimoto, Hiroyuki
    Hayashi, Tamio
    Ohshima, Takashi
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (04) : 499 - 502
  • [7] Rhodium/diene-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated Weinreb amides
    Shintani, R
    Kimura, T
    Hayashi, T
    CHEMICAL COMMUNICATIONS, 2005, (25) : 3213 - 3214
  • [8] Iridium/Chiral Diene-Catalyzed Asymmetric 1,6-Addition of Arylboroxines to α,β,γ,δ-Unsaturated Carbonyl Compounds
    Nishimura, Takahiro
    Yasuhara, Yuichi
    Sawano, Takahiro
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) : 7872 - +
  • [9] Carbon-carbon bond-forming enantioselective synthesis of chiral organosilicon compounds by rhodium/chiral diene-catalyzed asymmetric 1,4-addition reaction
    Shintani, R
    Okamoto, K
    Hayashi, T
    ORGANIC LETTERS, 2005, 7 (21) : 4757 - 4759
  • [10] Catalytic asymmetric synthesis of allylsilanes through rhodium/chiral diene-catalyzed 1,4-addition of alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes
    Shintani, Ryo
    Ichikawa, Yoshitaka
    Hayashi, Tamio
    Chen, Jinshui
    Nakao, Yoshiaki
    Hiyama, Tamejiro
    ORGANIC LETTERS, 2007, 9 (22) : 4643 - 4645
12345