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An Efficient Enantioselective Method for Asymmetric Friedel–Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes

✍ Scribed by Liang Hong; Lei Wang; Chao Chen; Bangzhi Zhang; Rui Wang

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
190 KB
Volume
351
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

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The Lewis base‐Lewis base bifunctional catalytic system has been developed and successfully applied to the asymmetric Friedel–Crafts alkylation of indoles with α,β‐unsaturated aldehydes. The reactions are promoted by chiral diphenylprolinol trimethylsilyl ether in the presence of triethylamine. By this protocol, optically active 3‐substituted indoles can be obtained in an organocatalytic process that is free of Lewis or protic acid in high yields with up to 98% ee. Besides, this reaction could be carried out on a gram scale without any loss in the enantioselectivity.

📜 SIMILAR VOLUMES

ChemInform Abstract: CaSH Organocatalysi
ChemInform Abstract: CaSH Organocatalysis: Enantioselective Friedel—Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes.
✍ Tian Tian; Bao-Jian Pei; Qing-Hua Li; Hao He; Ling-Yan Chen; Xiang Zhou; Wing-Ho 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 30 KB 👁 1 views

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