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Diels−Alder Exo Selectivity in Terminal-Substituted Dienes and Dienophiles: Experimental Discoveries and Computational Explanations
2009
Journal of the American Chemical Society
The Diels-Alder reactions of a series of silyloxydienes and silylated dienes with acyclic α,βunsaturated ketones and N-acyloxazolidinones have been investigated. The endo/exo stereochemical outcome is strongly influenced by the substitution pattern of the reactants. High exo selectivity was observed when the termini of the diene and the dienophile involved in the shorter forming bond are both substituted, while the normal endo preference was found otherwise. The exo-selective asymmetric
doi:10.1021/ja8079548
pmid:19154113
pmcid:PMC2635921
fatcat:zk6jgifbefabtfve3cnkcdvrw4