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Diastereoselective Cyclizations of 1,3-Dioxan-2-yl Radicals: Chiral Acyl Radical Equivalents

✍ Scribed by Bertrand, Michèle P.; Crich, David; Nouguier, Robert; Samy, Raghu; Stien, Didier


Book ID
125943666
Publisher
American Chemical Society
Year
1996
Tongue
English
Weight
164 KB
Volume
61
Category
Article
ISSN
0022-3263

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Chiral acyl radical equivalents: 5-exo c
✍ D. Stien; D. Crich; M.P. Bertrand 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 532 KB

Chiral 1,3-dioxolan-2-yl radicals derived from acetals 8 and 9 underwent intramolecular hydrogen abstraction followed by 5-exo-trig cyclization on treatment with tributyltin hydride and AIBN with modest and opposite stereoselectivities. The more highly substituted substrate 13 took part in a similar