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Stereochemistry of the [2+4] cycloaddition of cyclopentyne
Authors:John C. Gilbert  Duen-Ren Hou
Affiliation:a Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station Stop A5300, Austin, TX 78712, USA
b Department of Chemistry, National Central University. No. 300, Jung-Da Road, Jung-Li City, Taoyuan 320, Taiwan, ROC
Abstract:The [2+4] cycloaddition of cyclopentyne with a pair of diastereomeric 1,3-dienes is found to occur with high stereoselectivity. The results support the applicability of the principles of orbital symmetry even in the case of this exceedingly reactive dienophile.
Keywords:Cyclopentyne   Diels-Alder Reaction   Stereochemistry   Orbital symmetry
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