Scandium(III) triflate as an efficient and recyclable catalyst for chemoselective conversion of carbonyl compounds to 1,3-oxathiolanes

被引:26
|
作者
Karimi, B [1 ]
Ma'mani, L [1 ]
机构
[1] IASBS, Dept Chem, Gava Zang, Zanjan, Iran
来源
SYNTHESIS-STUTTGART | 2003年 / 16期
关键词
heterocycles; protecting groups; acetals; scandium; aldehydes; ketones; catalysis;
D O I
10.1055/s-2003-42436
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of carbonyl compounds can be easily and rapidly converted to the corresponding 1,3-oxathiolanes in the presence of a catalytic amount of scandium(III) triflate [Sc(OTf)(3)] in CH2Cl2. After completion of the reaction, the catalyst can straightforwardly be recovered using standard methods. Moreover, by employing this protocol, chemoselective oxathioacetalization of aldehydes in the presence of ketones can be achieved.
引用
收藏
页码:2503 / 2506
页数:4
相关论文
共 50 条
  • [31] An efficient and chemoselective method for synthesis of 1,3-oxathiolanes from aldehydes and their deprotection catalyzed by V(HSO4)3
    Shirini, F.
    Abedini, M.
    Ghasemi, M.
    Sakhaei, A.R.
    Bulletin of the Korean Chemical Society, 2009, 30 (10) : 2479 - 2480
  • [32] An Efficient and Chemoselective Method for Synthesis of 1,3-Oxathiolanes from Aldehydes and their Deprotection Catalyzed by V(HSO4)3
    Shirini, F.
    Abedini, M.
    Ghasemi, M.
    Sakhaei, A. R.
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (10): : 2479 - 2480
  • [33] Efficient regeneration of aldehydes from their corresponding 1,3-oxathiolanes in the absence of solvent
    Farhad Shirini
    Seyyedeh Kobra Mirhashemi
    Aysa Pourvali
    Masoumeh Abedini
    Chinese Chemical Letters, 2011, 22 (04) : 421 - 423
  • [34] Efficient regeneration of aldehydes from their corresponding 1,3-oxathiolanes in the absence of solvent
    Shirini, Farhad
    Mirhashemi, Seyyedeh Kobra
    Pourvali, Aysa
    Abedini, Masoumeh
    CHINESE CHEMICAL LETTERS, 2011, 22 (04) : 421 - 423
  • [35] Regeneration of carbonyl compounds from oximes, hydrazones, semicarbazones, acetals, 1,1-diacetates, 1,3-dithiolanes, 1,3-dithianes and 1,3-oxathiolanes
    Hajipour, AR
    Khoee, S
    Ruoho, AE
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2003, 35 (06) : 527 - +
  • [36] An exceptionally simple and catalytic method for regeneration of carbonyl functionality from the corresponding 1,3-oxathiolanes
    Mondal, E
    Sahu, PR
    Bose, G
    Khan, AT
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (08): : 1026 - 1028
  • [37] A dream combination for catalysis: highly reactive and recyclable scandium(III) triflate-catalyzed cyanosilylations of carbonyl compounds in an ionic liquid
    Park, Boyoung Y.
    Ryu, Ka Yeon
    Park, Jung Hwan
    Lee, Sang-gi
    GREEN CHEMISTRY, 2009, 11 (07) : 946 - 948
  • [38] Facile deprotection of 1,3-oxathiolanes to carbonyl compounds with O-iodoxy benzoic acid (IBX) in the presence of β-cyclodextrin in water
    Reddy, M. Somi
    Narender, M.
    Mahesh, A.
    Nageswar, Y. V. D.
    Rao, K. Rama
    SYNTHETIC COMMUNICATIONS, 2006, 36 (24) : 3771 - 3775
  • [39] Facile protection of carbonyl compounds as oxathiolanes and thioacetals promoted by PEG1000-based dicationic acidic ionic liquid as chemoselective and recyclable catalyst
    Ren, Yi-Ming
    Shao, Juan-Juan
    Wu, Zhi-Chuan
    Zhang, Shuai
    Tao, Ting-Xian
    JOURNAL OF MOLECULAR LIQUIDS, 2014, 196 : 392 - 394
  • [40] Scandium triflate as an efficient and recyclable catalyst for the deprotection of tert-butyl aryl sulfonamides
    Mahalingam, AK
    Wu, XY
    Wan, YQ
    Alterman, M
    SYNTHETIC COMMUNICATIONS, 2005, 35 (03) : 417 - 425