Rhodium-Catalyzed Asymmetric 1,4-Addition of α,β-Unsaturated Imino Esters Using Chiral Bicyclic Bridgehead Phosphoramidite Ligands

被引：51
|
作者：
Lee, Ansoo [1 ]
Kim, Hyunwoo [1 ,2 ]
机构：
[1] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 34141, South Korea
[2] Inst for Basic Sci Korea, Ctr Nanomat & Chem React, Taejon 34141, South Korea
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 35期
关键词：
PHOSPHINE-OLEFIN LIGANDS; BIS-SULFOXIDE LIGAND; ARYLBORONIC ACIDS; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; BORONIC ACIDS; ALKENYLBORONIC ACIDS; DIENE LIGANDS; DIELS-ALDER; ARYLATION;
D O I：
10.1021/jacs.5b07034
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A chiral bicyclic bridgehead phosphoramidite (briphos) prepared from 1-aminoindane is a highly efficient and selective ligand for rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated N,N-dimethyl-sulfamoyl imino esters at ambient temperature. This transformation provides a new class of chiral (Z)-gamma,gamma-diaryl-alpha,beta-dehydroamino esters with excellent yield and enantioselectivity.
引用
收藏
页码：11250 / 11253
页数：4
相关论文
共 50 条
  • [31] Heteroarylboronates in Rhodium-Catalyzed 1,4-Addition to Enones
    Albrecht, Fabian
    Sowada, Oliver
    Fistikci, Meryem
    Boysen, Mike M. K.
    ORGANIC LETTERS, 2014, 16 (19) : 5212 - 5215
  • [32] Mechanistic studies on the catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of aryltitanate reagents to α,β-unsaturated ketones
    Tokunaga, N
    Yoshida, K
    Hayashi, T
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5445 - 5449
  • [33] Easily accessible C2-symmetric chiral bicyclo[3.3.0] dienes as ligands for rhodium-catalyzed asymmetric 1,4-addition
    Feng, Chen-Guo
    Wang, Zhi-Qian
    Tian, Ping
    Xu, Ming-Hua
    Lin, Guo-Qiang
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1511 - 1516
  • [34] Asymmetric conjugate 1,4-addition of arylboronic acids to α,β-unsaturated esters catalyzed by rhodium(I)/(S)-binap
    Sakuma, S
    Sakai, M
    Itooka, R
    Miyaura, N
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19): : 5951 - 5955
  • [35] Enantio selective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds catalyzed by rhodium(I)-chiral phosphoramidite complexes
    Kurihara, Kazunori
    Sugishita, Noriyuki
    Oshita, Kengo
    Piao, Dongguo
    Yamamoto, Yasunori
    Miyaura, Norio
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (1-3) : 428 - 435
  • [36] Asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated aldehydes catalyzed by a chiral diene-rhodium complex
    Hayashi, T
    Tokunaga, N
    Okamoto, K
    Shintani, R
    CHEMISTRY LETTERS, 2005, 34 (11) : 1480 - 1481
  • [37] Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones
    Takaya, Y
    Ogasawara, M
    Hayashi, T
    Sakai, M
    Miyaura, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) : 5579 - 5580
  • [38] An N-Linked Bidentate Phosphoramidite Ligand (N-Me-BIPAM) for Rhodium-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Ketones
    Yamamoto, Yasunori
    Kurihara, Kazunori
    Takahashi, Yoshinori
    Miyaura, Norio
    MOLECULES, 2013, 18 (01) : 14 - 26
  • [39] Rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated amides
    Sakuma, S
    Miyaura, N
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26): : 8944 - 8946
  • [40] Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds:: Large accelerating effects of bases and ligands
    Itooka, R
    Iguchi, Y
    Miyaura, N
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15): : 6000 - 6004
12345