Journal of the Korean Magnetic Resonance Society (한국자기공명학회논문지)

Korean Magnetic Resonance Society (한국자기공명학회)
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NMR Signal Assignments of the Stereochemical Cycloadducts of Bicyclolactone via Diels-Alder Reaction

  • Kim, Dae-Sung (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University) ;
  • Seo, Chan-Woo (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University) ;
  • Cho, Cheon-Gyu (Department of Chemistry, College of Natural Sciences, Hanyang University) ;
  • Won, Ho-Shik (Department of Chemistry and Applied Chemistry, College of Science and Technology, Hanyang University)
  • Published : 2004.06.01
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Abstract

Bicyclolactones obtained from the Diels-Alder cycloaddition of 3,5-dibromo-2-pyrone can undergo various palladium catalyzed cross coupling reactions to afford aryl bicyclolactones. The resulting coupled products can be readily converted into various 3-OH cyclohexenes via lactone ring openings, while those bearing dienyl units underwent highly diastereoselective Diels-Alder cycloadditions with selected dienophiles to funish multiply functionalized polycarbocycles. Bromo-bicyclic diene furnished two different diastereomers endo-form (62%) and exo-form (38%) upon cycloadditions with N-Et maleimide (NEM), and their stereochemistries were identified with NMR.

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