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Amine-catalyzed direct self Diels–Alder reactions of α,β-unsaturated ketones in water: synthesis of pro-chiral cyclohexanones

✍ Scribed by D.B. Ramachary; Naidu S. Chowdari; Carlos F. Barbas III

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
87 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Amine-catalyzed direct self Diels-Alder reactions of a,b-unsaturated ketones have been developed. (S)-1-(2-Pyrrolidinyl-methyl)pyrrolidine, L-proline and pyrrolidine catalyzed the reaction of a,b-unsaturated ketones to provide cyclohexanone derivatives with good yield (up to 80%) in a single step via in situ-generation of 2-amino-1,3-butadienes and iminium ion-activated enones. Pro-chiral cyclohexanones were selectively prepared with pyrrolidine catalysis in water.

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✍ Rajeswari Thayumanavan; Buchiramachary Dhevalapally; Kandasamy Sakthivel; Fujie 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 76 KB

Amine-catalyzed Diels-Alder reactions of a,b-unsaturated ketones with dienophiles have been developed. Either (S)-1-(2-pyrrolidinylmethyl)pyrrolidine or L-proline catalyzed the in situ-generation and reaction of 2-amino-1,3-dienes to provide cyclohexanone derivatives in good yield (up to 87%) in one