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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 9
BKCSDE 31(9)
September 20, 2010 

Origin of Exo/Endo Selectivity in the Intramolecular Diels-Alder Reaction
Shihai Yan, Do Hyun Ryu, Jin Yong Lee*
Intramolecular Diels-Alder reaction, DFT, Selectivity, Orbital interaction, Steric repulsion
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.
2527 - 2530
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