ENANTIOSELECTIVE CYCLOPROPANATION OF ALLYLIC ALCOHOLS CATALYZED BY A CHIRAL DISULFONAMIDE-ALUMINUM COMPLEX

被引:55
|
作者
IMAI, N [1 ]
TAKAHASHI, H [1 ]
KOBAYASHI, S [1 ]
机构
[1] SAGAMI CHEM RES CTR, 4-4-1 NISHI OHNUMA, SAGAMIHARA, KANAGAWA 229, JAPAN
关键词
D O I
10.1246/cl.1994.177
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A chiral disulfonamide-alkylaluminum complex prepared from (1R,2R)-N,N'-bis(benzenesulfonyl)-1,2-cyclohexanediamine and trialkylaluminum or i-Bu2AlH has been found to catalyze a Simmons-Smith cyclopropanation of allylic alcohols with Et2Zn and CH2I2 to afford the corresponding cyclopropanes in excellent yields with high enantiomeric excesses.
引用
收藏
页码:177 / 180
页数:4
相关论文
共 50 条
  • [41] Nickel-catalyzed enantioselective hydrovinylation of silyl-protected allylic alcohols:An efficient access to homoallylic alcohols with a chiral quaternary center
    ZHANG QiZHU ShouFeiCAI YanWANG LiXin ZHOU QiLin State Key Laboratory and Institute of Elementoorganic ChemistryNankai UniversityTianjin China
    Science China(Chemistry), 2010, 53 (09) : 1899 - 1906
  • [42] Nickel-catalyzed enantioselective hydrovinylation of silyl-protected allylic alcohols: An efficient access to homoallylic alcohols with a chiral quaternary center
    Zhang Qi
    Zhu Shou-Fei
    Cai Yan
    Wang Li-Xin
    Zhou Qi-Lin
    SCIENCE CHINA-CHEMISTRY, 2010, 53 (09) : 1899 - 1906
  • [43] DESIGN OF AMPHOTERIC BIFUNCTIONAL LIGANDS - APPLICATION TO THE ENANTIOSELECTIVE SIMMONS-SMITH CYCLOPROPANATION OF ALLYLIC ALCOHOLS
    CHARETTE, AB
    JUTEAU, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2651 - 2652
  • [44] Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols
    Race, Nicholas J.
    Schwalm, Cristiane S.
    Nakamuro, Takayuki
    Sigman, Matthew S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) : 15881 - 15884
  • [45] Nickel-Catalyzed Enantioselective α-Allylation of Cyclic Ketones with Allylic Alcohols
    Jiang, Neng-Quan
    Li, Ming-Ming
    Xiao, Li-Jun
    Zhou, Qi-Lin
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (18) : 3829 - 3832
  • [46] Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols
    Sigman, Matthew S. (sigman@chem.utah.edu), 1600, American Chemical Society (138):
  • [47] Oxazaborolidine-catalyzed enantioselective reduction of α-methylene ketones to allylic alcohols
    Matsuo, Jun-ichi
    Kozai, Takaaki
    Nishikawa, Osamu
    Hattori, Yu
    Ishibashi, Hiroyuki
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6902 - 6904
  • [48] Organoiodine-Catalyzed Enantioselective Alkoxylation/Oxidative Rearrangement of Allylic Alcohols
    Zhang, Dong-Yang
    Zhang, Ying
    Wu, Hua
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (22) : 7450 - 7453
  • [49] Enantioselective iminium-catalyzed epoxidation of hindered trisubstituted allylic alcohols
    Novikov, Roman
    Lacour, Jerome
    TETRAHEDRON-ASYMMETRY, 2010, 21 (11-12) : 1611 - 1618
  • [50] Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid
    Bryliakov, KP
    Talsi, EP
    Kühn, T
    Bolm, C
    NEW JOURNAL OF CHEMISTRY, 2003, 27 (03) : 609 - 614