Intramolecular Diels-Alder reactions of cycloalkenones: stereoselectivity, Lewis acid acceleration, and halogen substituent effects.

The intramolecular Diels-Alder reactions of cycloalkenones and terminal dienes occur with high endo stereoselectivity, both thermally and under Lewis-acidic conditions. Through computations, we show that steric repulsion and tether conformation govern the selectivity of the reaction, and incorporati...

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Bibliographic Details
Main Authors: Pham, H, Paton, R, Ross, A, Danishefsky, S, Houk, K
Format: Journal article
Language:English
Published: 2014