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ChemInform Abstract: Base-Catalyzed Asymmetric Diels—Alder Reaction of 3-Hydroxy-2-pyrone and Simple Aryl Vinyl Sulfoxide: Asymmetric Synthesis of Carbaketopyranoses.

✍ Scribed by Hiroaki Okamura; Fumiya Urabe; Toshiyuki Hamada; Tetsuo Iwagawa

Book ID
115552202
Publisher
John Wiley and Sons
Year
2012
Weight
27 KB
Volume
43
Category
Article
ISSN
0931-7597

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Asymmetric base-catalyzed Diels-Alder re
Asymmetric base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral acrylate derivatives
✍ Hiroaki Okamura; Katsuki Morishige; Tetsuo Iwagawa; Munehiro Nakatani 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 200 KB

In the presence of a cinchona alkaloid as a catalyst, the Diels-Alder reaction of 3-hydroxy-2-pyrone with chiral N-acryloyl oxazolidinone afforded a bicyclolactone adduct with high diastereoselectivities (up to 95%de) in almost quantitative yield.