HIGHLY ENANTIOSELECTIVE SYNTHESIS OF PROPARGYLIC ALCOHOLS BY WAY OF THE ASYMMETRIC ALDOL REACTION

被引:17
|
作者
MUKAIYAMA, T
FURUYA, M
OHTSUBO, A
KOBAYASHI, S
机构
关键词
D O I
10.1246/cl.1991.989
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the presence of a catalytic amount of chiral diamine-coordinated tin(II) triflate, acetylenic aldehydes enantioselectively react with silyl enol ethers of thioesters to afford the corresponding aldol-type adducts, propargylic alcohols, in high yields. The products are easily converted to the corresponding optically active allene derivatives via effective chiral transfer.
引用
收藏
页码:989 / 992
页数:4
相关论文
共 50 条
  • [41] Enantioselective synthesis of propargylic alcohols by addition of enantiopure cyclopentadienyldialkoxyallyltitanium complexes to acetylenic aldehydes
    BouzBouz, S
    Pradaux, F
    Cossy, J
    Ferroud, C
    Falguières, A
    TETRAHEDRON LETTERS, 2000, 41 (46) : 8877 - 8880
  • [42] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes
    Frantz, DE
    Fässler, R
    Carreira, EM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1806 - 1807
  • [43] Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases
    Schubert, T
    Hummel, W
    Kula, MR
    Müller, M
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (22) : 4181 - 4187
  • [44] Catalytic Asymmetric Mannich-Ketalization Reaction: Highly Enantioselective Synthesis of Aminobenzopyrans
    Rueping, Magnus
    Lin, Ming-Yuan
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) : 4169 - 4172
  • [45] Highly enantioselective synthesis of a chiral 3-quinolylalkanol by an asymmetric autocatalytic reaction
    Shibata, T
    Choji, K
    Morioka, H
    Hayase, T
    Soai, K
    CHEMICAL COMMUNICATIONS, 1996, (06) : 751 - 752
  • [46] Carane amino alcohols as organocatalysts in asymmetric aldol reaction of isatin with acetone
    Banina, O. A.
    Sudarikov, D. V.
    Nigmatov, A. G.
    Frolova, L. L.
    Slepukhin, P. A.
    Zlotin, S. G.
    Kutchin, A. V.
    RUSSIAN CHEMICAL BULLETIN, 2017, 66 (02) : 293 - 296
  • [47] ENANTIOSELECTIVE SYNTHESIS OF SPIROOXINDOLES VIA DIRECT CATALYTIC ASYMMETRIC ALDOL-TYPE REACTION OF ISOTHIOCYANATO OXINDOLES
    Kato, Shota
    Kanai, Motomu
    Matsunaga, Shigeki
    HETEROCYCLES, 2014, 88 (01) : 475 - 491
  • [48] Asymmetric synthesis of tricyclic-cyclobutane by means of enantioselective deprotonation and intramolecular Michael-aldol reaction
    Takasu, K
    Misawa, K
    Ihara, M
    TETRAHEDRON LETTERS, 2001, 42 (48) : 8489 - 8491
  • [49] A simplified catalytic system for direct catalytic asymmetric aldol reaction of thioamides; application to an enantioselective synthesis of atorvastatin
    Kawato, Yuji
    Iwata, Mitsutaka
    Yazaki, Ryo
    Kumagai, Naoya
    Shibasaki, Masakatsu
    TETRAHEDRON, 2011, 67 (35) : 6539 - 6546
  • [50] Asymmetric aldol reaction of isatins with acetone in the presence of terpene amino alcohols
    Zlotin, Sergei G.
    Banina, Olga A.
    Sudarikov, Denis V.
    Nigmatov, Albert G.
    Frolova, Larisa L.
    Kutchin, Alexander V.
    MENDELEEV COMMUNICATIONS, 2020, 30 (02) : 147 - 149