Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones - Assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit.

• Author(s) / Creator(s)

  • Yu, Goujun
  • Clive, Derrick L. J.

• Conjugate addition of Me3SiMe2SiLi to cycloalk-2-en-1-ones, ketalization, Tamao-Fleming oxidation (Bu4NF, then H2O2, KHCO3), TPAP oxidation and acid hydrolysis generates 2-methyl cycloalkane-1,3-diones. Ketalization is needed in order to prevent addition of Me3Si- to the carbonyl. The pentamethyldisilanyl group has advantages over other silicon units that are used in Tamao-Fleming procedures.

• Date created

  2016-01-01

• Subjects / Keywords

  • Carbon-Silicon Bond
  • Organic-Sythesis
  • Stereoselective-Synthesis
  • Conjugate Addition
  • Oxidation
  • Ketones
  • Palladium
  • Reagents
  • Fragmentation
  • Garsubellin

• Type of Item

  Article (Draft / Submitted)

• DOI

  https://doi.org/10.7939/r3-9meb-wb22

• License

  Attribution-NonCommercial 4.0 International