Bronsted Acid-Catalyzed Dihydroxylation of Olefins in Aqueous Medium

被引:23
|
作者
Rosatella, Andreia A. [1 ]
Afonso, Carlos A. M. [1 ]
机构
[1] Univ Lisbon, Fac Farm, iMed UL, P-1649003 Lisbon, Portugal
关键词
dihydroxylation; 1; 2-diols; hydrogen peroxide; olefins; water; SPHINGOMONAS SP HXN-200; NONHEME IRON CATALYSTS; HYDROGEN-PEROXIDE; ENANTIOSELECTIVE HYDROLYSIS; TRANS DIHYDROXYLATION; CIS-DIHYDROXYLATION; ORGANIC-SOLVENT; DIOLS; OXIDATION; ALKENES;
D O I
10.1002/adsc.201100187
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The trans-dihydroxylation of olefins occurs efficiently by aqueous hydrogen peroxide catalyzed by p-toluenesulfonic acid at 50?degrees C, allowing the catalyst reuse and an outstanding substrate functional group tolerance such as tert-butoxycarbonylamino (BocNH), benzyloxycarbonylamino (CbzNH), benzyloxy (OBn), tosyloxy (OTs), hindered ketal, (2-trimethylsilyl)ethoxymethoxy (OSEM), benzylamino (NBz), benzyloxy (OBz) and free amino acid.
引用
收藏
页码:2920 / 2926
页数:7
相关论文
共 50 条
  • [11] Bronsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes
    Gicquiaud, Julien
    Abadie, Baptiste
    Dhara, Kalyan
    Berlande, Murielle
    Hermange, Philippe
    Sotiropoulos, Jean-Marc
    Toullec, Patrick Y.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (69) : 16266 - 16271
  • [12] On the Bronsted Acid-Catalyzed Homogeneous Hydrolysis of Furans
    Nikbin, Nima
    Caratzoulas, Stavros
    Vlachos, Dionisios G.
    CHEMSUSCHEM, 2013, 6 (11) : 2066 - 2068
  • [13] Mechanism of Bronsted Acid-Catalyzed Glucose Dehydration
    Yang, Liu
    Tsilomelekis, George
    Caratzoulas, Stavros
    Vlachos, Dionisios G.
    CHEMSUSCHEM, 2015, 8 (08) : 1334 - 1341
  • [14] THE MECHANISM OF THE ACID-CATALYZED HYDRATION OF OLEFINS
    LEVY, JB
    TAFT, RW
    HAMMETT, LP
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (05) : 1253 - 1254
  • [15] ACID-CATALYZED ADDITION OF PHOSPHINE TO OLEFINS
    HOFF, MC
    HILL, P
    JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (03): : 356 - 359
  • [16] Lewis and Bronsted acid-catalyzed allylsilane oligomerization
    Wigman, Benjamin
    Franz, Annaliese
    Armstrong, Brittany
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [17] Bronsted acid-catalyzed nucleophilic substitution of alcohols
    Sanz, Roberto
    Martinez, Alberto
    Miguel, Delia
    Alvarez-Gutierrez, Julia M.
    Rodriguez, Felix
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) : 1841 - 1845
  • [18] Bronsted acid-catalyzed amidation of imines.
    Antilla, JC
    Zhang, H
    Wang, Y
    Rowland, EB
    Rowland, GB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U390 - U390
  • [19] Mechanism of Bronsted acid-catalyzed conversion of carbohydrates
    Yang, Gang
    Pidko, Evgeny A.
    Hensen, Emiel J. M.
    JOURNAL OF CATALYSIS, 2012, 295 : 122 - 132
  • [20] SULFINIC ACID-CATALYZED ISOMERIZATION OF OLEFINS
    GIBSON, TW
    STRASSBURGER, P
    JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (05): : 791 - 793