Stereochemistry of the [2+4] cycloaddition of cyclopentyne

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. Graphic

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Bibliographic Details
Published in:Tetrahedron 2004-01, Vol.60 (2), p.469-474
Main Authors: Gilbert, John C., Hou, Duen-Ren
Format: Article
Language:English
Subjects:
Cyclopentyne
Diels–Alder Reaction
Orbital symmetry
Stereochemistry
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.11.003