Epoxidation of 4-Alkylidenecyclopentenones: A Route to the 1-Oxaspiro[2.4]hept-6-en-5-one Framework

被引：2
作者：
Ahmar, Mohammed [1 ]
Thome, Stephane [1 ]
Cazes, Bernard [1 ]
机构：
[1] Univ Lyon 1, CNRS UMR ICBMS 5246, Lab COSMO, F-69622 Villeurbanne, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 36期
关键词：
Synthetic methods; Epoxidation; Spiro compounds; PAUSON-KHAND REACTION; RING-CLOSURE; ACID; CONSTRUCTION;
D O I：
10.1002/ejoc.201201030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Thanks to their lack of polarity, the exocyclic double bonds of 4-alkylidenecyclopentenones 4 are selectively epoxidized by MCPBA to give spiroepoxycyclopentenones 7, which feature the nonclassical 1-oxaspiro[2.4]hept-6-en-5-one framework. Under acidic conditions, compounds 7 undergo ring-opening to afford 4-hydroxy-4-(1-hydroxyalkyl)cyclopentenones 10.
引用
收藏
页码：7093 / 7105
页数：13
相关论文
共 49 条
  • [1] CARBOPALLADATION OF ALLENIC HYDROCARBONS - A NEW WAY TO FUNCTIONALIZED STYRENES AND 1,3-BUTADIENES
    AHMAR, M
    BARIEUX, JJ
    CAZES, B
    GORE, J
    [J]. TETRAHEDRON, 1987, 43 (03) : 513 - 526
  • [2] Epoxidation of 4-alkylidenecyclopentenones
    Ahmar, M
    Thomé, S
    Cazes, B
    [J]. SYNLETT, 2006, (02) : 279 - 282
  • [3] PAUSON-KHAND REACTION WITH ALLENIC COMPOUNDS .1. SYNTHESIS OF 4-ALKYLIDENE-2-CYCLOPENTENONES
    AHMAR, M
    ANTRAS, F
    CAZES, B
    [J]. TETRAHEDRON LETTERS, 1995, 36 (25) : 4417 - 4420
  • [4] Syntheses of pentafulvenes from 4-alkylidenecyclopentenones
    Antras, F
    Ahmar, M
    Cazes, B
    [J]. TETRAHEDRON LETTERS, 2002, 43 (29) : 5029 - 5031
  • [5] Regioselectivity in the Pauson-Khand reaction of allenic hydrocarbons
    Antras, F
    Ahmar, M
    Cazes, B
    [J]. TETRAHEDRON LETTERS, 2001, 42 (46) : 8153 - 8156
  • [6] Pauson-Khand Reaction of Allenic Hydrocarbons: Synthesis of 4-Alkylidenecyclopentenones
    Antras, Frederic
    Laurent, Stephane
    Ahmar, Mohammed
    Chermette, Henry
    Cazes, Bernard
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (17) : 3312 - 3336
  • [7] Stereoselective synthesis of (E)-4-alkylidenecyclopent-2-en-1-ones by a tandem ring closure-Michael addition-elimination
    Ballini, R
    Bosica, G
    Fiorini, D
    Gil, MV
    Petrini, M
    [J]. ORGANIC LETTERS, 2001, 3 (09) : 1265 - 1267
  • [8] Bartok M., 1980, CHEM F ETHERS CROWN, P609
  • [9] Bauer T., 1995, HOUBEN WEYL METHODEN, VE21e, P4649
  • [10] GUAIANOLIDES RELATED TO ARBORESCIN FROM ARTEMISIA-ADAMSII
    BOHLMANN, F
    HARTONO, L
    JAKUPOVIC, J
    HUNECK, S
    [J]. PHYTOCHEMISTRY, 1985, 24 (05) : 1003 - 1007
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