On the palladium(II)-catalysed oxidative rearrangement of propargylic acetates

被引:17
作者
Bartels, A [1 ]
Mahrwald, R [1 ]
Müller, K [1 ]
机构
[1] Humboldt Univ, Inst Chem, D-12489 Berlin, Germany
关键词
oxidation; palladium; rearrangement;
D O I
10.1002/adsc.200303200
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The catalytic transformation of propargylic acetates into the corresponding alpha-acetoxyenones in the presence of palladium(II) chloride is described. Water is a necessary component in this unusual oxidative rearrangement.
引用
收藏
页码:483 / 485
页数:3
相关论文
共 21 条
[1]  
BLY RS, 1969, J AM CHEM SOC, V91, P3289
[2]   ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP [J].
BURGESS, K ;
JENNINGS, LD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6129-6139
[3]   Synthesis of optically active allenes using tandem enzyme and palladium-catalysed reactions [J].
Dixneuf, PH ;
Guyot, T ;
Ness, MD ;
Roberts, SM .
CHEMICAL COMMUNICATIONS, 1997, (21) :2083-2084
[4]   UBER METHYLENDESOXYBENZOINE .4. UBER DIE UMLAGERUNG VON ACETYLEN-GAMMA-GLYKOLEN MIT ACETYLCHLORID [J].
FIESSELMANN, H ;
SASSE, K .
CHEMISCHE BERICHTE-RECUEIL, 1956, 89 (07) :1775-1791
[5]   EPIMERIZATION OF MESTRANOL ACETATE ON ALUMINA [J].
KANOJIA, RM ;
YARMCHUC.L ;
SCHEER, I .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) :2304-2306
[6]   PALLADIUM(II)-CATALYZED OXIDATIVE REARRANGEMENT OF PROPARGYL ESTERS [J].
KATAOKA, H ;
WATANABE, K ;
GOTO, K .
TETRAHEDRON LETTERS, 1990, 31 (29) :4181-4184
[7]   A SHORT AND EFFICIENT SYNTHETIC METHOD FOR THE CORTICOSTEROID SIDE-CHAIN FROM 17-KETO STEROIDS [J].
KATAOKA, H ;
WATANABE, K ;
MIYAZAKI, K ;
TAHARA, S ;
OGU, K ;
MATSUOKA, R ;
GOTO, K .
CHEMISTRY LETTERS, 1990, (09) :1705-1708
[8]   The tautomerism of alpha diketones I Benzyl phenyl diketone [J].
Kohler, EP ;
Barnes, RP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :211-214
[9]   PALLADIUM(II)-INDUCED CONVERSION OF ALPHA-ACETOXYALKYNES INTO ALPHA,BETA-UNSATURATED ALPHA-ACETOXYKETONES - A NOVEL ACCESS TO ALPHA-DIKETONES [J].
MAHRWALD, R ;
SCHICK, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (05) :593-594
[10]   TiCl4-mediated nucleophilic substitution of propargylic esters [J].
Mahrwald, R ;
Quint, S .
TETRAHEDRON, 2000, 56 (38) :7463-7468