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
  • [31] Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(III) metal complex
    Tak, Rajkumar
    Kumar, Manish
    Kureshy, Rukhsana I.
    Choudhary, Manoj Kumar
    Khan, Noor-Ul H.
    Abdi, Sayed H. R.
    Bajaj, Hari C.
    RSC ADVANCES, 2016, 6 (09): : 7693 - 7700
  • [32] Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model
    Zhang, W
    Basak, A
    Kosugi, Y
    Hoshino, Y
    Yamamoto, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (28) : 4389 - 4391
  • [33] Enantioselective palladium catalyzed allylic substitution with chiral pyridine ligands
    Chelucci, G
    Caria, V
    Saba, A
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 130 (1-2) : 51 - 55
  • [34] Chiral Bronsted acid catalyzed enantioselective intermolecular allylic aminations
    Zhuang, Minyang
    Du, Haifeng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (26) : 4590 - 4593
  • [35] Nickel-Catalyzed Enantioselective Alkylative Coupling of Alkynes and Aldehydes: Synthesis of Chiral Allylic Alcohols with Tetrasubstituted Olefins
    Yang, Yun
    Zhu, Shou-Fei
    Zhou, Chang-Yue
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (43) : 14052 - +
  • [36] Enantioselective acylations of alcohols catalyzed by chiral phosphines.
    Daugulis, O
    Vedejs, E
    Diver, ST
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 444 - ORGN
  • [37] Diastereoselective zinco-cyclopropanation of chiral allylic alcohols with gem-dizinc carbenoids
    Fournier, JF
    Mathieu, S
    Charette, AB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) : 13140 - 13141
  • [39] Vanadium-catalyzed enantioselective desymmetrization of meso secondary allylic alcohols and homoallylic alcohols
    Li, Zhi
    Zhang, Wei
    Yamamoto, Hisashi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7520 - 7522
  • [40] Nickel-catalyzed enantioselective hydrovinylation of silyl-protected allylic alcohols: An efficient access to homoallylic alcohols with a chiral quaternary center
    Qi Zhang
    Shou-Fei Zhu
    Yan Cai
    Li-Xin Wang
    Qi-Lin Zhou
    Science China Chemistry, 2010, 53 : 1899 - 1906