Modular Two-Step Approach for the Stereodivergent Synthesis of 1,3-Diamines with Three Continuous Stereocenters

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• 作者：Juliette Halli ; Michael Bolte ; Jan Bats ; Georg Manolikakes
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：674-677
• 全文大小：372K
• ISSN：1523-7052

文摘

A two-step reaction sequence for the highly stereodivergent construction of 1,3-diamines with three continuous stereocenters is reported. This novel method enables the controlled synthesis of any given diastereomer of the 1,3-diamine scaffold from a simple set of starting materials in a highly modular manner. The disclosed approach is based on the reaction of an enamide with an in situ generated N-acylimine followed by a subsequent trapping of the generated intermediate with a suitable nucleophile. By careful choice of starting materials, reagents, and reaction conditions, each stereocenter can be constructed in a highly selective fashion.