Synthesis of Chiral Sulfamide-Amine Alcohol Ligands for Enantioselective Alkylation of Aldehydes

被引:10
|
作者
Mao, Jincheng [1 ]
机构
[1] Suzhou Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
基金
中国国家自然科学基金;
关键词
Amine alcohols; asymmetric addition; diethylzinc; enantioselectivities; ASYMMETRIC ADDITIONS; ORGANOZINC REAGENTS; DIETHYLZINC; BENZALDEHYDE; ALKYNYLATION; DIALKYLZINC; ORIGIN;
D O I
10.1080/00397910902806265
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of chiral sulfamide-amine alcohols (SAA) (1-6) has been easily synthesized from commercially available chiral amino alcohols. In the absence of Ti(OiPr)4, ligand 4 catalyzed the asymmetric addition of diethylzinc to aromatic aldehydes with moderate to good yields and enantioselectivities.
引用
收藏
页码:3710 / 3721
页数:12
相关论文
共 50 条
  • [31] Functionalized organolithium reagents in the synthesis of chiral ligands for catalytic enantioselective addition of diethylzinc to aldehydes
    Dobrikov, Georgi M.
    Philipova, Irena
    Nikolova, Rositsa
    Shivachev, Boris
    Chimov, Angel
    Dimitrov, Vladimir
    POLYHEDRON, 2012, 45 (01) : 126 - 143
  • [32] Catalytic enantioselective arylation of aryl aldehydes by chiral aminophenol ligands
    Yang, Xiao-Feng
    Hirose, Takuji
    Zhang, Guang-You
    TETRAHEDRON-ASYMMETRY, 2009, 20 (04) : 415 - 419
  • [33] Enantioselective addition of diethylzinc to aldehydes in the presence of chiral aprotic ligands
    Jin, MJ
    Kim, YM
    Lee, KS
    TETRAHEDRON LETTERS, 2005, 46 (15) : 2695 - 2696
  • [34] Enantioselective diethylzinc additions to aldehydes catalyzed by chiral relay ligands
    Sibi, MP
    Stanley, LM
    TETRAHEDRON-ASYMMETRY, 2004, 15 (21) : 3353 - 3356
  • [35] Enantioselective alkynylation of aromatic aldehydes catalyzed by readily available chiral amino alcohol-based ligands
    Li, Z
    Upadhyay, V
    DeCamp, AE
    DiMichele, L
    Reider, PJ
    SYNTHESIS-STUTTGART, 1999, : 1453 - 1458
  • [36] AN EFFICIENT AND ENANTIOSELECTIVE SYNTHESIS OF A CHIRAL PRIMARY AMINE
    SON, YC
    PARK, CH
    KOH, JS
    CHOY, NY
    LEE, CS
    CHOI, H
    KIM, SC
    YOON, HS
    TETRAHEDRON LETTERS, 1994, 35 (22) : 3745 - 3746
  • [37] The synthesis of chiral amino diol tridentate ligands and their enantioselective induction during the addition of diethylzinc to aldehydes
    Zhang, An-lin
    Yang, Li-wen
    Yang, Nian-fa
    Liu, Yan-ling
    TETRAHEDRON-ASYMMETRY, 2014, 25 (04) : 289 - 297
  • [38] Synthesis of Chiral Tridentate Ligands Embodying the Bispidine Framework and Their Application in the Enantioselective Addition of Diethylzinc to Aldehydes
    Zhang, Yuecheng
    Gao, Jingyuan
    Shi, Naiyue
    Zhao, Jiquan
    ADVANCES IN CHEMICAL ENGINEERING, PTS 1-3, 2012, 396-398 : 1236 - 1243
  • [39] Direct Regiospecific and Highly Enantioselective Intermolecular a-Allylic Alkylation of Aldehydes by a Combination of Transition-Metal and Chiral Amine Catalysts
    Afewerki, Samson
    Ibrahem, Ismail
    Rydfjord, Jonas
    Breistein, Palle
    Cordova, Armando
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) : 2972 - 2977
  • [40] Enantioselective Synthesis of Succinimides by Michael Addition of Aldehydes to Maleimides Organocatalyzed by Chiral Primary Amine-Guanidines
    Avila, Angel
    Chinchilla, Rafael
    Gomez-Bengoa, Enrique
    Najera, Carmen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) : 5085 - 5092