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A switch of enantiofacial selectivity in chiral ytterbium-catalyzed 1,3-dipolar cycloaddition reactions

✍ Scribed by Mikako Kawamura; Shū Kobayashi

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
197 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

Synthesis of both enantiomers of the 1,3-dipolar cycloaddition adducts between nitrones and alkenes has been achieved using the same chiral ytterbium catalyst choosing achiral additives, nitrone and MS 4A.

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Lanthanide triflate catalyzed 1,3-dipolar cycloaddition reactions: stereoselective synthesis of indenoisoxazolidines
✍ David A Nugiel 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 55 KB

Substituted indenones reacted smoothly with a variety of in situ generated nitrones in the presence of lanthanide triflates to give exclusive exo 1,3-dipolar cycloaddition products in high yield. Judicious choice of the nitrone substituents allowed for further modification of the indenoisoxazolidine