Bulletin of the Korean Chemical Society

  • 제31권9호
  • /
  • Pages.2527-2530
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 투고 : 2010.06.07
  • 심사 : 2010.07.16
  • 발행 : 2010.09.20
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초록

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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