Cu(OTf)2-catalyzed selective opening of aryl and vinyl epoxides with carbonyl compounds to give 1,3-dioxolanes

被引:12
|
作者
Krasik, P [1 ]
Bohemier-Bernard, M [1 ]
Yu, Q [1 ]
机构
[1] Shire BioChem Inc, Laval, PQ H7V 4A7, Canada
关键词
epoxide-opening; dioxolanes; copper triflate; chemoselectivity;
D O I
10.1055/s-2005-864795
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper(II) triflate catalyzes the ring-opening of aryl- and vinyl-substituted epoxides with various carbonyl compounds to furnish 1,3-dioxolanes under mild conditions. Alkyl- and alkoxy-carbonyl-substituted epoxides remain unchanged under reaction conditions. This allows selective opening of aryl-substituted epoxides in the presence of alkyl-substituted ones.
引用
收藏
页码:854 / 856
页数:3
相关论文
共 50 条
  • [1] Conversion of epoxides to 1,3-dioxolanes catalyzed by tin(II) chloride
    Vyvyan, JR
    Meyer, JA
    Meyer, KD
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 9144 - 9147
  • [2] Efficient conversion of epoxides to 1,3-dioxolanes catalyzed by bismuth(III) salts
    Mohammadpoor-Baltork, I
    Khosropour, AR
    Aliyan, H
    SYNTHETIC COMMUNICATIONS, 2001, 31 (22) : 3411 - 3416
  • [3] Conversion of epoxides to 1,3-dioxolanes catalyzed by tin(II) chloride.
    Vyvyan, JR
    Meyer, JA
    Meyer, KD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U342 - U342
  • [4] Cu(OTf)2-catalyzed ring-opening of epoxides with anilines:A convenient synthesis of β-amino alcohols
    侯雪龙
    吴劼
    戴立信
    Chinese Journal of Chemistry, 1998, (06) : 557 - 560
  • [5] Cu(OTf)2-catalyzed ring-opening of epoxides with anilines:: A convenient synthesis of β-amino alcohols
    Hou, XL
    Wu, J
    Dai, LX
    CHINESE JOURNAL OF CHEMISTRY, 1998, 16 (06) : 557 - 560
  • [6] Efficient and catalytic conversion of epoxides to 1,3-dioxolanes with TiO(TFA)2 or TiCl3(OTf)
    Iranpoor, N
    Zeynizadeh, B
    JOURNAL OF CHEMICAL RESEARCH-S, 1998, (08): : 466 - 467
  • [7] Isomerization of 2-vinyl-1,3-dioxolanes and 2-vinyl-1,3-dioxanes catalyzed by ruthenium complexes
    Krompiec, S
    MaslinskaSolich, J
    Suwinski, J
    Macionga, A
    POLISH JOURNAL OF CHEMISTRY, 1996, 70 (08) : 1087 - 1090
  • [8] Cu(OTf)2-Catalyzed efficient sulfonylation of vinyl azides with sodium sulfinates
    Ning, Zhitao
    Xu, Zheng
    Liu, Ruikai
    Du, Zhengyin
    SYNTHETIC COMMUNICATIONS, 2021, 51 (22) : 3492 - 3500
  • [9] SYNTHESIS OF 1,3-DIOXOLANES BY REACTION OF CIS-ALPHA, EPOXYCYCLOALKANOL WITH CARBONYL-COMPOUNDS
    IWAHASHI, T
    MATSUBARA, F
    YOSHIHIRO, Y
    NIPPON KAGAKU KAISHI, 1982, (07) : 1193 - 1198
  • [10] Cu(OTf)2-catalyzed Et3SiH-reductive etherification of various carbonyl compounds with trimethylsilyl ethers
    Yang, WC
    Lu, XA
    Kulkarni, SS
    Hung, SC
    TETRAHEDRON LETTERS, 2003, 44 (42) : 7837 - 7840