Organocatalytic Enantioselective Michael–Henry Acetalization of Glutaraldehyde and 3‐Aryl‐2‐nitroprop‐2‐enols: A Facile Entry to 3‐Oxabicyclo[3.3.1]nonan‐2‐ones with Four Consecutive Stereogenic Centers

作者: Bor-Cherng Hong , Ding-Jyun Lan , Nitin S. Dange , Gene-Hsiang Lee , Ju-Hsiou Liao

DOI: 10.1002/EJOC.201201496

关键词: ChemistryOrganic chemistryOrganocatalysisMichael reactionStereocenterGlutaraldehydeNitroaldol reactionEnantioselective synthesisAryl

摘要: A convenient method was developed for the enantioselective (>99 % ee) synthesis of 3-oxabicyclo[3.3.1]nonan-2-ones containing four consecutive stereogenic centers. The comprises a cascade organocatalytic Michael–Henry acetalization–oxidation reaction glutaraldehyde and 3-aryl-2-nitroprop-2-enols. structures absolute configurations products were confirmed by X-ray analysis.

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