ChemInform Abstract: Sulfoxide-Mediated Diastereoselective Michael Additions. New Enantioselective Synthesis of C-4 Substituted 2-Pyroaminoadipic Acids.

✍ Scribed by Hassan Acherki; Carlos Alvarez-Ibarra; Alicia Barrasa; Alfonso de Dios

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199941137

✦ Synopsis

Sulfoxide-Mediated Diastereoselective Michael Additions. New Enantioselective Synthesis of C-4 Substituted 2-Pyroaminoadipic Acids.

-The aza-enolate of the homochiral sulfoxide (I) undergoes diastereoselective Michael reaction with the substituted acrylates (II) to yield dihydropyridones (III). The enantiomerically pure derivative (IIIa) can be easily converted to the C-4 substituted pyroaminoadipate (V). Interestingly, the above aza-enolate also adds to ethyl propiolates (VI) to obtain the homochiral pyrimidones (VII). -(ACHERKI, HASSAN; ALVAREZ-IBARRA, CARLOS; BARRASA, ALICIA;