Synthesis of C2-symmetric sulfide and its first application in highly enantioselective synthesis of chiral aziridines

被引:10
|
作者
Gui, Yuan [1 ]
Shen, Sheng [1 ]
Wang, Hai-Yang [1 ]
Li, Zhi-Yi [1 ]
Huang, Zhi-Zhen [1 ]
机构
[1] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Peoples R China
关键词
D O I
10.1246/cl.2007.1436
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A C-2-symmetric sulfide 6 has been synthesized from cheap L-tartaric acid. It was found that sulfide 6 could perform a tandem reaction with benzyl bromide and tosyl imines to give (2S.3S)-aziridines 9a-9g with good to excellent enantioseletivities (up to 96% ee).
引用
收藏
页码:1436 / 1437
页数:2
相关论文
共 50 条
  • [1] Synthesis and Application of C2-Symmetric Chiral Diol on the Enantioselective Addition of Diethylzinc to Aldehydes
    王锐
    杨晓武
    沈健恒
    达朝山
    粟武
    王恒山
    陈新滋
    [J]. 厦门大学学报(自然科学版), 1999, (S1) : 161 - 161
  • [2] Synthesis of a C2-symmetric chiral bipyridyldiol ligand and its application in the enantioselective addition of diethylzine to substituted benzaldehydes
    Chen, YJ
    Lin, RX
    Chen, CP
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (22) : 3561 - 3571
  • [3] Synthesis of Chiral Tetrahydroisoquinoline and C2-Symmetric Bistetrahydroisoquinoline Ligands and Their Application in the Enantioselective Henry Reaction
    Duc Thinh Khong
    Judeh, Zaher M. A.
    [J]. SYNTHESIS-STUTTGART, 2016, 48 (14): : 2271 - 2279
  • [4] Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones
    Kawai, Hiroyuki
    Kusuda, Akihiro
    Mizuta, Satoshi
    Nakamura, Shuichi
    Funahashi, Yasuhiro
    Masuda, Hideki
    Shibata, Norio
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (08) : 762 - 765
  • [5] Simple enantioselective total synthesis of glabrescol, a chiral C2-symmetric pentacyclic oxasqualenoid
    Xiong, ZM
    Corey, EJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) : 9328 - 9329
  • [6] Enantioselective synthesis of DIANANE, a novel C2-symmetric chiral diamine for asymmetric catalysis
    Berkessel, A
    Schröder, M
    Sklorz, CA
    Tabanella, S
    Vogl, N
    Lex, J
    Neudörfl, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09): : 3050 - 3056
  • [7] Synthesis of C2-Symmetric Bisphosphines and Their Application in Enantioselective Transition Metal Catalysis
    Gok, Halil Zeki
    Kilicarslan, Seda
    Gok, Yasar
    [J]. CROATICA CHEMICA ACTA, 2018, 91 (01) : 89 - 97
  • [8] Synthesis of novel C2-symmetric chiral bis(oxazoline) ligands and their application in the enantioselective addition of diethylzinc to aldehydes
    Fu, B
    Du, DM
    Wang, JB
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (01) : 119 - 126
  • [9] Synthesis of chiral C2-symmetric binucleating ligands
    Fahrni, CJ
    Pfaltz, A
    [J]. HELVETICA CHIMICA ACTA, 1998, 81 (03) : 491 - 506
  • [10] Highly efficient, enantioselective synthesis of (+)-grandisol from a C2-symmetric bis(α,β-butenolide)
    de March, P
    Figueredo, F
    Font, J
    Raya, J
    [J]. ORGANIC LETTERS, 2000, 2 (02) : 163 - 165