Origin of Exo/Endo Selectivity in the Intramolecular Diels-Alder Reaction 


Vol. 31,  No. 9, pp. 2527-2530, Sep.  2010
10.5012/bkcs.2010.31.9.2527


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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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  Cite this article

[IEEE Style]

S. Yan, D. H. Ryu, J. Y. Lee, "Origin of Exo/Endo Selectivity in the Intramolecular Diels-Alder Reaction," Bulletin of the Korean Chemical Society, vol. 31, no. 9, pp. 2527-2530, 2010. DOI: 10.5012/bkcs.2010.31.9.2527.

[ACM Style]

Shihai Yan, Do Hyun Ryu, and Jin Yong Lee. 2010. Origin of Exo/Endo Selectivity in the Intramolecular Diels-Alder Reaction. Bulletin of the Korean Chemical Society, 31, 9, (2010), 2527-2530. DOI: 10.5012/bkcs.2010.31.9.2527.