Lewis-Base-Catalyzed Asymmetric Allylation of Isatins with Allyltrichlorosilane.

• Tác giả: Frederic Ballaschk, Adrián Gómez-Suárez, Stefan F Kirsch, Andreas F Kotthaus, Yasemin Özkaya, Christian Wagner
• Ngôn ngữ: eng
• Ký hiệu phân loại: 341.725 Military installations and bases
• Thông tin xuất bản: United States : Organic letters , 2025
• Bộ sưu tập: NCBI
• ID: 723280
• Chủ đề: 1. Lewis; 2. Base; 3. Catalyzed

Tóm tắt

Herein we report the enantioselective synthesis of 3-allyl-3-hydroxyoxindoles, a core scaffold in a wide range of bioactive molecules, using a Lewis-base catalyst and readily abundant and inexpensive allyltrichlorosilane. This transition-metal-free protocol employs relatively low catalyst loadings of a privileged bispyrrolidine-type scaffold to achieve high yields and enantioselectivities (up to 98% yield and 98:2 er). The total syntheses of the natural products (-)-flustraminol B and (-)-chimonamidine were also successfully carried out using our newly developed method as a key step, highlighting the potential of this method for the efficient and precise synthesis of complex natural products.