Tetrahedron Letters p. 2715 - 2718 (1991)
Update date:2022-07-30
Topics:
Shea, K. J.
Staab, Andrew J.
Zandi, Kathleen S.
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.
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