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标题:Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst
时间:2019-12-03 20:25:29
DOI:10.1016/j.tetasy.2014.01.005
作者:Zhao, Bo-Liang; Du, Da-Ming
关键词:pyran derivatives;diastereoselective syntheses, enantioselective syntheses (incl. cis/trans‐isomerism;ring closure reactions;organocatalysis
出版源: 《Tetrahedron Asymmetry》 ,25 (4) :310-317
摘要:The enantioselective tandem Michael addition reaction of dimedone and related 1,3-dicarbonyl compounds with alpha,beta-unsaturated N-acylated succinimides catalyzed by a chiral squaramide catalyst has been investigated. This reaction provides a new approach for the synthesis of chiral enol lactones in good yields with moderate to high enantioselectivities (up to 88% ee) through the enantioselective Michael addition followed by lactonization and removal of the succinimide auxiliary. (C) 2014 Elsevier Ltd. All rights reserved.
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目录:
  • Enantioselective synthesis of enol lactones from tandem Michael addition/lactonization catalyzed by a chiral squaramide catalyst
    • 1 Introduction
    • 2 Results and discussion
    • 3 Conclusion
    • 4 Experimental
      • 4.1 General
      • 4.2 Materials
        • 4.2.1 Synthesis of organocatalysts II
        • 4.2.2 General procedure for the preparation of α
      • 4.3 General procedure for the enantioselective synthesis of enol lactones
        • 4.3.1 (R)-7,7-Dimethyl-4-phenyl-4,6,7,8-tetrahydro-3H-chro- mene-2,5-dione 3a8
        • 4.3.2 (S)-4-(2-Chlorophenyl)-7,7-dimethyl-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 3b20
        • 4.3.3 (R)-4-(4-Bromophenyl)-7,7-dimethyl-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 3c8
        • 4.3.4 (R)-4-(4-Methoxyphenyl)-7,7-dimethyl-4,6,7,8-tetrahy- dro-3H-chromene-2,5-dione 3d
        • 4.3.5 (R)-7,7-Dimethyl-4-(4-nitrophenyl)-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 3e
        • 4.3.6 (R)-7,7-Dimethyl-4-(p-tolyl)-4,6,7,8-tetrahydro-3H-chro- mene-2,5-dione 3f
        • 4.3.7 (S)-7,7-Dimethyl-4-(furan-2-yl)-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 3g8
        • 4.3.8 (S)-4,7,7-Trimethyl-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 3h8
        • 4.3.9 (S)-4-Ethyl-7,7-dimethyl-4,6,7,8-tetrahydro-2H-chromene- 2,5-dione 3i8
        • 4.3.10 (S)-7,7-Dimethyl-4-propyl-4,6,7,8-tetrahydro-3H-chro- mene-2,5-dione 3j8
        • 4.3.11 (R)-4-Phenyl-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 5a
        • 4.3.12 (S)-4-Methyl-4,6,7,8-tetrahydro-3H-chromene-2,5-dione 5b8
        • 4.3.13 (R)-4-Phenyl-3,4-dihydropyrano[3,2-c]chromene-2,5-dione 7a8
        • 4.3.14 (S)-4-Methyl-3,4-dihydropyrano[3,2-c]chromene-2,5-dione 7b8
        • 4.3.15 (R)-7-Methyl-4-(p-tolyl)-3,4-dihydropyrano[4,3-b]pyran-2,5-dione 9a
        • 4.3.16 (S)-4,7-Dimethyl-3,4-dihydropyrano[4,3-b]pyran-2,5-dione 9b8
        • 4.3.17 (R)-5-Acetyl-3,4-dihydro-6-methyl-4-phenylpyran-2-one 11a21
    • Acknowledgments
    • References

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