Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Origin of Exo/Endo Selectivity in the Intramolecular Diels-Alder Reaction

  • Yan, Shihai (Department of Chemistry, Sungkyunkwan University) ;
  • Ryu, Do-Hyun (Department of Chemistry, Sungkyunkwan University) ;
  • Lee, Jin-Yong (Department of Chemistry, Sungkyunkwan University)
  • Received : 2010.06.07
  • Accepted : 2010.07.16
  • Published : 2010.09.20
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Abstract

The stereoselectivity of the intramolecular Diels-Alder reactions of 1 and its derivatives were investigated by ab initio calculations. The stereoselectivity mainly originates from the steric repulsion and the orbital interactions. The additional s-cis and s-trans conformations by introducing the carbonyl group at the neighbor of diene or dienophile may change the stereoselectivity, hence this kind of substitution can be utilized for stereoselectivive asymmetric synthesis.

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References

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