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Abstract
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.
Content
Supplementary material
Supporting Information
Experimental procedures, analytical data, copies of 1H and 13 NMR spectra
Computational data
optimized geometries, associated electronic energies and thermal corrections for fall calculated structures
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)
