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Effect of dienophile activating group on the stereoselectivity of the intramolecular diels-alder reaction

✍ Scribed by William R Roush; Amy P Essenfeld; Joseph S Warmus

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
276 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

The stereoselectivity of the intramolecular Diels-Alder reactions of terminally activated trienes 4 and 3 increases as the dienophile activating group is changed along the series -CONR2 < -C02Me < -COMe < -Cl-IO. Further increases in selectivity are realized by using Lewis acid catalysts.

These results are consistent with predictions based on the nonsynchronous transition state hypothesis.

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