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Intramolecular Diels–Alder reactions using chiral ruthenium Lewis acids and application in the total synthesis of ent-ledol

✍ Scribed by Thamapipol, Sirinporn; Kündig, E. Peter

Book ID
121427047
Publisher
Royal Society of Chemistry
Year
2011
Tongue
English
Weight
394 KB
Volume
9
Category
Article
ISSN
1477-0520

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Cationic bis(oxazoline)Cu(II) Lewis acid catalysts. Enantioselective furan Diels-Alder reaction in the synthesis of ent-shikimic acid
✍ David A. Evans; David M. Barnes 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 153 KB

The highly enantioselective Diels-Alder reaction between acryloyl oxazolidinone and furan, catalyzed by cationic bis(4-tert-butyloxazoline)Cu(II) complex 1, is presented. Though the reaction equilibrates rapidly at -20 °C, reaction at -78 °C permits isolation of the kinetic product mixture. The synt