Solid-Supported Odorless Reagents for the Dithioacetalization of Aldehydes and Ketones

被引：25
|
作者：
Jung, N. [1 ]
Graessle, S.
Luetjohann, S.
Braese, S.
机构：
[1] Karlsruhe Inst Technol, D-76344 Eggenstein Leopoldshafen, Germany
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 04期
关键词：
SULFURIC-ACID; CHEMOSELECTIVE DITHIOACETALIZATION; CARBONYL-COMPOUNDS; REUSABLE CATALYST; THIOACETALIZATION; EFFICIENT;
D O I：
10.1021/ol403313h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A solid supported, odorless reagent for the dithioacetalization of aldehydes and ketones has been developed. The new reagent provides the dimercaptoalkane equivalent in combination with stoichiometric amounts of immobilized acid and enables the formation of dithianes and dithiolanes from aldehydes without any additives in good to very good yields with high purities. The reaction is chemoselective for aldehydes, but ketones can be reacted to the corresponding dithioketals if an additional Lewis acid such as BF3 is added.
引用
收藏
页码：1036 / 1039
页数：4
相关论文
共 50 条
  • [1] Solid-supported reagents for the oxidation of aldehydes to carboxylic acids
    Takemoto, T
    Yasuda, K
    Ley, SV
    SYNLETT, 2001, (10) : 1555 - 1556
  • [2] Solid-supported reagents in organic synthesis
    Drewry, DH
    Coe, DM
    Poon, S
    MEDICINAL RESEARCH REVIEWS, 1999, 19 (02) : 97 - 148
  • [3] Surface crystallization of solid-supported reagents
    Stewart, Martin V.
    Mauritson, Amy E.
    Newsome, Anthony L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
  • [4] SOLID-SUPPORTED REAGENTS IN THE DETERMINATION OF CANNABINOIDS IN PLASMA
    ROSENFELD, JM
    MCLEOD, RA
    FOLTZ, RL
    ANALYTICAL CHEMISTRY, 1986, 58 (04) : 716 - 721
  • [5] Solid-supported Pd(0): an efficient heterogeneous catalyst for aerobic oxidation of benzyl alcohols into aldehydes and ketones
    Bandna
    Aggarwal, Nidhi
    Das, Pralay
    TETRAHEDRON LETTERS, 2011, 52 (38) : 4954 - 4956
  • [6] Solid-Supported Iodine(V) Reagents in Organic Synthesis
    Bensberg, Kathrin
    Gomez-Suarez, Adrian
    Kirsch, Stefan F.
    CHEMISTRY-A EUROPEAN JOURNAL, 2025,
  • [7] Synthesis and olefination of carbonyl compounds using solid-supported reagents
    Hansen, Anne-Lene L.
    Murray, Anthony
    Tanner, David
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (24) : 4497 - 4505
  • [8] Solid-supported reagents, catalysts and their use to solution phase synthesis
    Zhang, Liang
    Liu, Gang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (07) : 885 - 898
  • [9] Solid-supported Reagents in Organic Synthesis Using Microwave Irradiation
    Heravi, Majid M.
    Moghimi, Setareh
    CURRENT ORGANIC CHEMISTRY, 2013, 17 (05) : 504 - 527
  • [10] A total synthesis of epothilones using solid-supported reagents and scavengers
    Storer, RI
    Takemoto, T
    Jackson, PS
    Ley, SV
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (22) : 2521 - 2525
12345