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  • One-pot enantioselective syntheses of iminosugar derivatives using organocatalytic anti-michael-anti-aza-Henry reactions.

One-pot enantioselective syntheses of iminosugar derivatives using organocatalytic anti-michael-anti-aza-Henry reactions.

Organic letters (2010-11-03)
Ritsuo Imashiro, Hisatoshi Uehara, Carlos F Barbas
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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Sigma-Aldrich
(tert-Butyldimethylsilyloxy)acetaldehyde, 90%