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Studies of Diastereoselectivity in Diels−Alder Reactions of Enantiopure (S S )-2-( p -Tolylsulfinyl)-1,4-naphthoquinone and Chiral Racemic Acyclic Dienes

✍ Scribed by Carreño, M. Carmen; García-Cerrada, Susana; Urbano, Antonio; Di Vitta, Claudio


Book ID
125483280
Publisher
American Chemical Society
Year
2000
Tongue
English
Weight
116 KB
Volume
65
Category
Article
ISSN
0022-3263

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Regiochemical control in asymmetric Diel
✍ M.Carmen Carreño; JoséL García Ruano; Cynthia Z Remor; Antonio Urbano; Jean Fisc 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 243 KB

Enantiopure sulfinylquinones (+)-2 and (+)-3 reacted with Dane's diene 1 under thermal and ZnBr 2 Lewis acid conditions with reversal regiochemistry but similar ~-facial diastereoselectivity to afford, after spontaneous elimination of the sulfinyl group, tetracyclic derivatives 4-9.