135908-69-9Relevant academic research and scientific papers
Pericyclic Umpolung. Reversal of Regioselectivity in the Diels-Alder Reaction
Shea, K. J.,Staab, Andrew J.,Zandi, Kathleen S.
, p. 2715 - 2718 (2007/10/02)
New methodology is reported which enables reversal of regiochemistry in the Diels-Alder reaction.Esterification of 2-(β-hydroxyethyl)dimethylsilyldienes with common dienophiles followed by type 2 intramolecular Diely-Alder reaction results in formation of a single regio- and stereoisomer.Oxidative cleavage of the cycloadduct produces a cyclohexanone with a substitution pattern opposite of that found in the analogous bimolecular cycloaddition reaction.
