Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand

被引:11
|
作者
Miura, Tsuyoshi [1 ]
Itoh, Keisuke [1 ]
Yasaku, Yumi [1 ]
Koyata, Naka [1 ]
Murakami, Yasuoki [1 ]
Imai, Nobuyuki [1 ]
机构
[1] Chiba Inst Sci, Fac Pharmaceut Sci, Chiba 2880025, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/j.tetlet.2008.07.125
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclopropanation of allylic alcohols with Et(2)Zn and CH(2)I(2) in the presence of a catalytic amount of fluorous disulfonamide 3 afforded the corresponding cyclopropylmethanols in 69-96% yield with 49-83% ee. The fluorous ligand 3 was readily recovered from the reaction mixture by the fluorous solid-phase extraction (FSPE) and could be reused without a significant loss of the catalytic activity and enantioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5813 / 5815
页数:3
相关论文
共 50 条
  • [11] Catalytic Enantioselective Dibromination of Allylic Alcohols
    Hu, Dennis X.
    Shibuya, Grant M.
    Burns, Noah Z.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 12960 - 12963
  • [12] Catalytic Enantioselective Alkylations with Allylic Alcohols
    Bandini, Marco
    Cera, Gianpiero
    Chiarucci, Michel
    SYNTHESIS-STUTTGART, 2012, 44 (04): : 504 - 512
  • [13] Enantioselective cyclopropanation of allylic alcohols. The effect of zinc iodide
    Denmark, SE
    OConnor, SP
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10): : 3390 - 3401
  • [14] Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications
    Charette, AB
    Juteau, H
    Lebel, H
    Molinaro, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (46) : 11943 - 11952
  • [15] Syntheses of (R)-(+)-cibenzoline and analogues via catalytic enantioselective cyclopropanation using (S)-phenylalanine-derived disulfonamide
    Miura, Tsuyoshi
    Murakami, Yasuoki
    Imai, Nobuyuki
    TETRAHEDRON-ASYMMETRY, 2006, 17 (22) : 3067 - 3069
  • [16] Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: Scope of the cyclopropanation reaction
    Charette, AB
    Molinaro, C
    Brochu, C
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (49) : 12168 - 12175
  • [17] Catalytic asymmetric cyclopropanation of allylic alcohols with titanium-TADDOLate: Scope of the cyclopropanation reaction
    Charette, A.B.
    Molinaro, C.
    Brochu, C.
    1600, American Chemical Society (123):
  • [18] Catalytic, enantioselective dibromination of allylic alcohols: A computational perspective
    Pemberton, Ryan
    Hu, Dennis
    Burns, Noah
    Tantillo, Dean
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [19] Catalytic enantioselective epoxidation of tertiary allylic and homoallylic alcohols
    Yamamoto, H. (yamamoto@uchicago.edu), 1600, American Chemical Society (135):
  • [20] Catalytic Enantioselective Epoxidation of Tertiary Allylic and Homoallylic Alcohols
    Olivares-Romero, Jose Luis
    Li, Zhi
    Yamamoto, Hisashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (09) : 3411 - 3413