Theoretical Insight into the Reversal of Chemoselectivity in Diels-Alder Reactions of α,β-Unsaturated Aldehydes and Ketones Catalyzed by Brønsted and Lewis Acids
نویسندگان
چکیده
Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, reaction gave adduct derived from ketone major product. On other hand, use tris(pentafluorophenyl)borane B(C6F5)3 bulky Lewis catalyst mainly cycloadduct aldehyde Our aim present work is to put evidence role (2E)-but-2-enal 2-Hexen-4-one The calculations were performed at ωB97XD/6-311G(d,p) level theory solvent effects dichloromethane taken into account PCM solvation model. obtained results are good agreement experimental outcomes.
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ژورنال
عنوان ژورنال: Organics
سال: 2021
ISSN: ['2673-401X']
DOI: https://doi.org/10.3390/org2010004