Modular Two-Step Approach for the Stereodivergent Synthesis of 1,3-Diamines with Three Continuous Stereocenters
Juliette Halli1, Michael Bolte1, Jan Bats1
1Department of Biochemistry, Chemistry and Pharmacy, Goethe-University , Max-von-Laue-Strasse 7, 60438 Frankfurt, Germany.
Abstract:
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.
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