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