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A Convenient Synthesis of 2,2-Diallylated Nitrogen Heterocycles by Allylboration of Lactams

✍ Scribed by Yuri N. Bubnov; Fedor V. Pastukhov; Ilia V. Yampolsky; Anatoli V. Ignatenko


Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
217 KB
Volume
2000
Category
Article
ISSN
1434-193X

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Reductive 1,2-Allylboration of Indoles b
✍ YuryΒ N. Bubnov; IlyaΒ V. Zhun'; ElenaΒ V. Klimkina; AnatolyΒ V. Ignatenko; ZoyaΒ A. πŸ“‚ Article πŸ“… 2000 πŸ› John Wiley and Sons 🌐 English βš– 265 KB πŸ‘ 1 views

Indoles undergo reductive Ξ±-allylation upon treatment with allylic boranes (triallyl-and triprenylborane) to give, after deboronation, the corresponding 2-allylated indolines in 70-85% yield. 1,2-Addition of the allylboron fragment to heterocycles occurs with full rearrangement of the allylic moiety