Highly diastereoselective addition of alkoxyethynyl aluminium reagents to N-tert-butylsulfinyl aldimines

被引:12
|
作者
Verrier, Charlie [1 ]
Carret, Sebastien [1 ]
Poisson, Jean-Francois [1 ]
机构
[1] Univ Grenoble 1, Dept Chim Mol SERCO, UMR CNRS 5250, ICMG FR 2607, F-38041 Grenoble 9, France
关键词
REGIOSELECTIVE CLEAVAGE; ASYMMETRIC ADDITION; ALKYNYLATION; EPOXIDES; ALCOHOLS;
D O I
10.1039/c3ob42352b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of dimethylaluminium alkoxyacetylides to Ellman's sulfinylimines is described. The reaction proceeds with excellent diastereoselectivity and high yield to produce oxygenated propargylamines in one step starting from simple dichloroenol ethers.
引用
收藏
页码:1875 / 1878
页数:4
相关论文
共 50 条
  • [1] Indium-mediated diastereoselective addition of allyl bromides to enantiomerically pure N-tert-butylsulfinyl aldimines
    Foubelo, F
    Yus, M
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (24) : 3823 - 3825
  • [2] Highly Diastereoselective Synthesis of α-Difluoromethyl Amines from N-tert-Butylsulfinyl Ketimines and Difluoromethyl Phenyl Sulfone
    Liu, Jun
    Hu, Jinbo
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) : 11443 - 11454
  • [3] Ru-Catalyzed highly diastereoselective hydrogenation of N-tert-butylsulfinyl ketimines for the synthesis of aryl glycine derivatives
    Wei, Qiaoling
    Zhang, Feng
    Zhao, Xiaofang
    Wang, Chao
    Xiao, Jianliang
    Tang, Weijun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (26) : 5468 - 5471
  • [4] Diastereoselective Addition of Metal α-Fluoroenolates of Carboxylate Esters to N-tert-Butylsulfinyl Imines: Synthesis of α-Fluoro-β-amino Acids
    Shang, Huaqi
    Li, Ya
    Li, Xiang
    Ren, Xinfeng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8739 - 8747
  • [5] Highly diastereoselective addition of chiral H-phosphonate to tert-butylsulfinyl aldimines: a convenient approach to (R)-α-aminophosphonic
    Olszewski, Tomasz K.
    Majewski, Mateusz
    [J]. TETRAHEDRON-ASYMMETRY, 2015, 26 (15-16) : 846 - 852
  • [6] Chiral N-tert-Butylsulfinyl Imines: New Discoveries
    Foubelo, Francisco
    Yus, Miguel
    [J]. CHEMICAL RECORD, 2021, 21 (06): : 1300 - 1341
  • [7] Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines
    Alberto Sirvent, Juan
    Foubelo, Francisco
    Yus, Miguel
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03): : 1356 - 1367
  • [8] Base-promoted diastereoselective addition of nitromethane and nitroethane to N-tert-butylsulfinyl imines: synthesis of N-protected α-amino acids and amino ketones
    Jesus Garcia-Munoz, M.
    Dema, Haythem K.
    Foubelo, Francisco
    Yus, Miguel
    [J]. TETRAHEDRON-ASYMMETRY, 2014, 25 (04) : 362 - 372
  • [9] Synthesis of fluorinated chiral amines using N-tert-butylsulfinyl imines
    Liu, Jun
    Hu, Jinbo
    [J]. FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) : 875 - 888
  • [10] Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an α-chloroimine
    Hodgson, David M.
    Kloesges, Johannes
    Evans, Brian
    [J]. ORGANIC LETTERS, 2008, 10 (13) : 2781 - 2783