Stereocontrolled Assembly of Cis or Trans Angularly Substituted Hydrindenes by the Unactivated Intramolecular Diels−Alder Reaction
The Journal of Organic Chemistry1996Vol. 61(21), pp. 7508–7512
Citations Over TimeTop 13% of 1996 papers
Abstract
The unactivated intramolecular Diels-Alder reaction has become a powerful tool for the construction of polycyclic natural products. Nevertheless, the factors that govern diastereoselectivity in these cyclizations have not been fully understood. We here report that through the choice of the proper substituents, it is possible to make the unactivated intramolecular Diels-Alder reaction proceed to give either the cis angularly-substituted hydrindene 12b or the trans product 19a.
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