title: Modular Two-Step Approach for the Stereodivergent Synthesis of 1,3-Diamines with Three Continuous Stereocenters.
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.
authors.affiliation: Department of Biochemistry, Chemistry and Pharmacy, Goethe-University , Max-von-Laue-Strasse 7, 60438 Frankfurt, Germany.
authors.forename: Juliette
authors.initials: J
authors.lastname: Halli
authors.affiliation: Department of Biochemistry, Chemistry and Pharmacy, Goethe-University , Max-von-Laue-Strasse 7, 60438 Frankfurt, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Bolte
authors.affiliation: Department of Biochemistry, Chemistry and Pharmacy, Goethe-University , Max-von-Laue-Strasse 7, 60438 Frankfurt, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Bats
authors.affiliation: Department of Biochemistry, Chemistry and Pharmacy, Goethe-University , Max-von-Laue-Strasse 7, 60438 Frankfurt, Germany.
authors.forename: Georg
authors.identifier: 0000-0002-4013-5757
authors.initials: G
authors.lastname: Manolikakes