Organic Chemistry

Stereoselective Synthesis of 2-Oxyenamides



An improved route for the highly stereoselective synthesis of (Z)-2-oxyenamides is reported. The desired products can be accessed in only three steps from aminoacetaldehyde dimethyl acetal as common, readily available building block in a highly modular fashion. The improved procedure has been applied to the synthesis of various acylated and sufonylated oxyenamides. Mechanistic and theoretical studies provide a conclusive rationale for the observed stereoselectivities.


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Supplementary material

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Supporting Information
Experimental procedures, analytical data, copies of 1H and 13 NMR spectra
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Computational data
optimized geometries, associated electronic energies and thermal corrections for fall calculated structures
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X-Ray Data
cif and checkcif files for compounds 1a (CCDC 2180323), E-11c (CCDC 2180324), Z-11c (CCDC 2180325) and Z-12 (CCDC 2180326)