AI Article Synopsis
- The study demonstrates a one-pot reaction where organocatalysts facilitate asymmetric anti-Michael reactions using (tert-butyldimethylsilyloxy)acetaldehyde and various nitroolefins.
- This is followed by an intermolecular aza-Henry reaction with imine, yielding iminosugar derivatives featuring five contiguous stereocenters with high enantiomeric excess.
- The stereochemistry of the aza-Henry reaction is determined by the substrate and is supported by a six-membered cyclic transition-state model.
Article Abstract
Organocatalyst-controlled asymmetric anti-Michael reactions of (tert-butyldimethylsilyloxy)acetaldehyde with a range of nitroolefins, followed by an intermolecular aza-Henry reaction with imine, provided iminosugar derivatives with five contiguous stereocenters in very high enantiomeric excess in one pot. The stereochemistry of the aza-Henry reaction was substrate controlled and is explained by a six-membered cyclic transition-state model.
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| http://dx.doi.org/10.1021/ol102292a | DOI Listing |
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