A chiral acrylate equivalent for metal-free Diels-Alder reactions: endo-2-Acryloylisoborneol

…, JM García, A González, A Lecumberri…

Index: Palomo, Claudio; Oiarbide, Mikel; Garcia, Jesus M.; Gonzalez, Alberto; Lecumberri, Ainara; Linden, Anthony Journal of the American Chemical Society, 2002 , vol. 124, # 35 p. 10288 - 10289

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Citation Number: 28

Abstract

The principle of metal-free activation of enones toward the Diels-Alder reaction with dienes is demonstrated by exploiting the capability of Brønsted acids to activate α'-hydroxyenones through hydrogen bonding. The diastereoselective application of such a principle is nicely realized by using a newly designed family of camphor-based chiral enones, which upon catalytic action of either trifluoroacetic or triflic acid lead to the corresponding cycloadducts ...

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