Asymmetric synthesis of 2-alkyl-4-hydroxycyclohex-2-en-1-ones by scandium(III) triflate-catalyzed fragmentation of 2-alkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones

被引：1
|
作者：
Matsuo, Jun-ichi [1 ]
Kawano, Mizuki [1 ]
Takeuchi, Kosuke [1 ]
Tanaka, Hiroyuki [1 ]
Ishibashi, Hiroyuki [1 ]
机构：
[1] Kanazawa Univ, Coll Med Pharmaceut & Hlth Sci, Sch Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 17期
关键词：
Fragmentation; Acid catalysis; Chiral building block; LEWIS-ACID CATALYSTS; FORMAL SYNTHESIS; 2-CROTONYLOXYMETHYL-(4R,5R,6R)-4,5,6-TRIHYDROXYCYCLOHEX-2-ENONE COTC; ENANTIOSELECTIVE ROUTE; PLATENSIMYCIN; ANALOGS;
D O I：
10.1016/j.tetlet.2009.02.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Fragmentation of (2S,3S,4S)-2-allyl-3-iodo-1-oxocyclohexan-2,4-carbolactone to (4S)-2-allyl-4-hydroxy-cyclohex-2-en-1-one, a chiral building block of (-)-platensimycin, proceeded efficiently by using scandium(III) triflate in DMF-H2O (1:3) at 100 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1917 / 1919
页数：3
相关论文
共 50 条
  • [1] Novel fragmentation reaction of 2-alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones
    Khim, SK
    Dai, MS
    Zhang, XQ
    Chen, L
    Pettus, L
    Thakkar, K
    Schultz, AG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22): : 7728 - 7733
  • [2] Ammonia-promoted fragmentation of 2-alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones
    Dai, MS
    Zhang, XQ
    Khim, SK
    Schultz, AG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01): : 384 - 387
  • [3] Asymmetric synthesis and fragmentation reactions of 2-alkyl- and 2,4-dialkyl-3-iodo-1-oxocyclohexan-2,4-carbolactones.: Single enantiomer preparation of Δα,β-butenolides, 2-alkyl-4-hydroxy-2-cyclohexen-1-ones and butyrolactones.
    Schultz, AG
    Dai, MS
    Khim, SK
    Pettus, LP
    Thakkar, K
    [J]. TETRAHEDRON LETTERS, 1998, 39 (24) : 4203 - 4206
  • [4] Stereoselective dihydroxylation of 2-alkyl- and 2,4-dialkyl-2-amido-3-cyclohexen-1-ones. Synthesis of enantiomerically related 2-alkyl- and 2,4-dialkyl-3-hydroxy-1-oxocyclohexan-2,4-carbolactones by complementary butyrolactonization reactions
    Schultz, AG
    Dai, MS
    Tham, FS
    Zhang, XQ
    [J]. TETRAHEDRON LETTERS, 1998, 39 (37) : 6663 - 6666
  • [5] SYNTHESIS OF ALKYL-CYCLOBUT-2-EN-3-OL-1-ONES
    CORBELLA, A
    GARIBOLD.P
    JOMMI, G
    [J]. CHEMISTRY & INDUSTRY, 1968, (28) : 948 - &
  • [6] Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols
    Salgado, A
    Dejaegher, Y
    Verniest, G
    Boeykens, M
    Gauthier, C
    Lopin, C
    Tehrani, KA
    De Kimpe, N
    [J]. TETRAHEDRON, 2003, 59 (13) : 2231 - 2239
  • [7] SYNTHESIS OF SOME 2-ALKYL CYCLOALK-2-EN-1-ONES
    SINGH, VS
    GUPTA, SML
    [J]. CURRENT SCIENCE, 1981, 50 (18): : 816 - 816
  • [8] ALKYL SUBSTITUTED 3-METHYLCYCLOHEX-2-EN-1-ONES
    MCANDREW, BA
    [J]. JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS, 1977, 28 (10): : 629 - 639
  • [9] Mercuric triflate-catalyzed synthesis of 2-methylfurans from 1-alkyn-5-ones
    Imagawa, H
    Kurisaki, T
    Nishizawa, M
    [J]. ORGANIC LETTERS, 2004, 6 (21) : 3679 - 3681
  • [10] Recyclable gallium(III) triflate-catalyzed [4+3] cycloaddition for synthesis of 2,4-disubstituted-3H-benzo[b][1,4]diazepines
    Huang, Shi-Gang
    Mao, Hai-Feng
    Zhou, Shao-Fang
    Zou, Jian-Ping
    Zhang, Wei
    [J]. TETRAHEDRON LETTERS, 2013, 54 (46) : 6178 - 6180
12345