CHEMOSELECTIVE AND REGIOSELECTIVE ISOMERIZATION OF EPOXIDES TO CARBONYL-COMPOUNDS VIA PALLADIUM CATALYSIS

被引:63
|
作者
KULASEGARAM, S [1 ]
KULAWIEC, RJ [1 ]
机构
[1] GEORGETOWN UNIV,DEPT CHEM,WASHINGTON,DC 20057
来源
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 24期
关键词
D O I
10.1021/jo00103a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium(O)-tertiary phosphine complexes catalyze the chemo- and regioselective isomerization of epoxides to carbonyl compounds in good to excellent yields; alkyl-substituted epoxides afford methyl ketones, and aryl-substituted epoxides form aldehydes or ketones via cleavage of the benzylic C-O bond.
引用
收藏
页码:7195 / 7196
页数:2
相关论文
共 50 条
  • [21] DEMONSTRATION OF NEED FOR ELECTROPHILIC CATALYSIS IN ADDITION OF ORGANOLITHIUM COMPOUNDS TO CARBONYL-COMPOUNDS
    PIERRE, JL
    HANDEL, H
    PERRAUD, R
    TETRAHEDRON LETTERS, 1977, (23) : 2013 - 2014
  • [22] SELECTIVE REDUCTION OF CARBONYL-COMPOUNDS BY HETEROGENEOUS CATALYSIS ON SALT SURFACES
    BOYER, J
    CORRIU, RJP
    PERZ, R
    REYE, C
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (03) : 121 - 122
  • [23] SELECTIVE REDUCTION OF CARBONYL-COMPOUNDS BY HETEROGENEOUS CATALYSIS ON SALT SURFACES
    BOYER, J
    CORRIU, RJP
    PERZ, R
    REYE, C
    TETRAHEDRON, 1981, 37 (11) : 2165 - 2171
  • [24] REGIOSELECTIVITY IN ELECTROCHEMICAL ALLYLATION OF CARBONYL-COMPOUNDS - A SYNTHESIS OF EGOMAKETONE BY REGIOSELECTIVE ALLYLATION
    TOKUDA, M
    SATOH, S
    SUGINOME, H
    JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23): : 5608 - 5613
  • [25] THE MECHANISM OF THE PALLADIUM-CATALYZED REACTION OF ALLYLIC ACETATES WITH CARBONYL-COMPOUNDS VIA ELECTROCHEMICAL REDUCTION
    ZHANG, PP
    ZHANG, WC
    ZHANG, TF
    WANG, ZQ
    ZHOU, WJ
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) : 491 - 492
  • [26] ALLYLBARIUM REAGENTS - UNPRECEDENTED REGIOSELECTIVE AND STEREOSELECTIVE ALLYLATION REACTIONS OF CARBONYL-COMPOUNDS
    YANAGISAWA, A
    HABAUE, S
    YASUE, K
    YAMAMOTO, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6130 - 6141
  • [27] REDUCTION OF CARBONYL-COMPOUNDS VIA HYDROSILYLATION .1. HYDROSILYLATION OF CARBONYL-COMPOUNDS CATALYZED BY TRIS(TRIPHENYLPHOSPHINE)CHLORORHODIUM
    OJIMA, I
    NIHONYANAGI, M
    KOGURE, T
    KUMAGAI, M
    HORIUCHI, S
    NAKATSUGAWA, K
    NAGAI, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 94 (03) : 449 - 461
  • [28] HIGHLY CHEMOSELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS WITH TETRAALLYLTIN IN ACIDIC AQUEOUS-MEDIA
    YANAGISAWA, A
    INOUE, H
    MORODOME, M
    YAMAMOTO, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10356 - 10357
  • [29] Regioselective Addition of Quinoline Derivatives to Carbonyl Compounds via Palladium-Catalyzed Umpolung with Diethylzinc
    Matsumoto, Yohei
    Yamamoto, Kosuke
    Kuriyama, Masami
    Nishida, Koyo
    Onomura, Osamu
    SYNTHESIS-STUTTGART, 2019, 51 (08): : 1795 - 1802
  • [30] Multiple arylation of alkyl aryl ketones and α,β-unsaturated carbonyl compounds via palladium catalysis
    Terao, Y
    Kametani, Y
    Wakui, H
    Satoh, T
    Miura, M
    Nomura, M
    TETRAHEDRON, 2001, 57 (28) : 5967 - 5974