Stereoselective Synthesis of 2-Oxyenamides

23 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

enamides
DFT calculations
synthetic methods
enolate
Z-selective

Supplementary materials

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