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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| http://dx.doi.org/10.1021/acs.orglett.6b03841 | DOI Listing |
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