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Stereoselective Reduction of Methyl Vinyl Ketone Dimer

  • Published : 1990.08.20

Abstract

The stereoselectivity of the reaction between methyl vinyl ketone dimer, which contains two possible sites of chelation, and zinc borohydride or diisobutylaluminum hydride has been studied in order to illuminate the factors involved in the high levels of asymmetric induction obtained in the bicyclic system. The conditions for the formation of the exo-5,7-dimethyl-6,8-dioxabicyclo[3.2.1]octane are DIBAH reduction of MVK dimer in ether at reflux followed by acidic cyclizatioan, and for the endo isomer are $Zn(BH_4)_2$ reduction with $ZnCl_2$ at $0^{\circ}C.$.

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Cited by

  1. ChemInform Abstract: Stereoselective Reduction of Methyl Vinyl Ketone Dimer. vol.22, pp.3, 1990, https://doi.org/10.1002/chin.199103069
  2. Study on the Development of Catalyst System for the Novel Rearrangement Reaction of Bicyclic Ketal Compound vol.28, pp.13, 1990, https://doi.org/10.1080/00397919808004301
  3. Visible light photocatalysis of radical anion hetero-Diels-Alder cycloadditions vol.67, pp.24, 1990, https://doi.org/10.1016/j.tet.2011.02.066