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

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.