An extremely powerful acylation reaction of alcohols with acid anhydrides catalyzed by trimethylsilyl trifluoromethanesulfonate

被引:282
作者
Procopiou, PA [1 ]
Baugh, SPD [1 ]
Flack, SS [1 ]
Inglis, GGA [1 ]
机构
[1] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1021/jo980011z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trimethylsilyl trifluoromethanesulfonate is an excellent catalyst for the acylation of alcohols with acid anhydrides. Highly functionalized primary, secondary, tertiary, and allylic alcohols, and phenols, were acylated cleanly and efficiently and in a fraction of the time used under the standard DMAP conditions.
引用
收藏
页码:2342 / 2347
页数:6
相关论文
共 56 条
  • [1] ISOKINETIC TEMPERATURE OF ACYLATION OF L-MENTHOL
    AKIYAMA, F
    TOKURA, N
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1968, 41 (11) : 2690 - +
  • [2] BORON FLUORIDE PROMOTED OPENING OF EPOXIDES BY ORGANOCOPPER AND CUPRATE REAGENTS
    ALEXAKIS, A
    JACHIET, D
    NORMANT, JF
    [J]. TETRAHEDRON, 1986, 42 (20) : 5607 - 5619
  • [3] SPECIFIC REACTIVITY OF THE O-(BETA-D-GLUCOPYRANOSYL-(1-]6)-D-GLUCOPYRANOSE) LINKAGE WITH ACETIC-ANHYDRIDE IN THE PRESENCE OF TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
    ANGIBEAUD, P
    BOSSO, C
    UTILLE, JP
    [J]. CARBOHYDRATE RESEARCH, 1990, 198 (02) : 403 - 407
  • [4] STEREOSELECTIVE REACTION OF METHYL ALPHA-D-GLYCOPYRANOSIDE AND BETA-D-GLYCOPYRANOSIDE WITH ACETIC-ANHYDRIDE IN THE PRESENCE OF TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE
    ANGIBEAUD, P
    UTILLE, JP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (05): : 1490 - 1492
  • [5] CHEMISTRY OF CEPHALOSPORIN ANTIBIOTICS .2. PREPARATION OF A NEW CLASS OF ANTIBIOTICS AND RELATION OF STRUCTURE TO ACTIVITY
    CHAUVETTE, RR
    SPENCER, JL
    MUELLER, RA
    ROESKE, RW
    MORIN, RB
    RYAN, CW
    JACKSON, BG
    PIOCH, RP
    FLYNN, EH
    VANHEYNINGEN, E
    LAVAGNINO, ER
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (17) : 3401 - &
  • [6] CHEMISTRY OF CEPHALOSPORIN ANTIBIOTICS .V. AMIDES AND ESTERS OF CEPHALOTHIN
    CHAUVETTE, RR
    FLYNN, EH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1966, 9 (05) : 741 - +
  • [7] EMDE H, 1982, SYNTHESIS-STUTTGART, P1
  • [8] A REGIOSELECTIVE AND STEREOSPECIFIC SYNTHESIS OF ALLYLSILANES FROM SECONDARY ALLYLIC ALCOHOL DERIVATIVES
    FLEMING, I
    HIGGINS, D
    LAWRENCE, NJ
    THOMAS, AP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24): : 3331 - 3349
  • [9] ALKOXYNITRENIUM ION CYCLIZATIONS - EVIDENCE FOR DIFFERENT MECHANISMS IN THE FORMATION OF BENZOXAZINES AND BENZOXAZEPINES
    GLOVER, SA
    ROWBOTTOM, CA
    SCOTT, AP
    SCHOONRAAD, JL
    [J]. TETRAHEDRON, 1990, 46 (20) : 7247 - 7262
  • [10] ANTIOXIDANT-BASED INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS - THE DISCOVERY OF 6-[1-[2-(HYDROXYMETHYL)PHENYL]-1-PROPEN-3-YL]-2,3-DIHYDRO-5-BENZOFURANOL, A POTENT TOPICAL ANTIINFLAMMATORY AGENT
    HAMMOND, ML
    ZAMBIAS, RA
    CHANG, MN
    JENSEN, NP
    MCDONALD, J
    THOMPSON, K
    BOULTON, DA
    KOPKA, IE
    HAND, KM
    OPAS, EE
    LUELL, S
    BACH, T
    DAVIES, P
    MACINTYRE, DE
    BONNEY, RJ
    HUMES, JL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (03) : 908 - 918