Catalytic Asymmetric Mannich Reactions of Sulfonylacetates

Sulfone versus sulfone: Arylsulfonylacetates can be viewed as synthetic equivalents of a variety of α‐carboxylate anions. Phase‐transfer catalysis (PTC) enabled their mild deprotonation and catalytic asymmetric addition to highly reactive imines generated in situ from α‐amidosulfones (see scheme; Pg...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (31), p.5694-5697
Hauptverfasser: Cassani, Carlo, Bernardi, Luca, Fini, Francesco, Ricci, Alfredo
Format: Artikel
Sprache:eng
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Zusammenfassung:Sulfone versus sulfone: Arylsulfonylacetates can be viewed as synthetic equivalents of a variety of α‐carboxylate anions. Phase‐transfer catalysis (PTC) enabled their mild deprotonation and catalytic asymmetric addition to highly reactive imines generated in situ from α‐amidosulfones (see scheme; Pg=protecting group). The synthetic utility of the products was demonstrated by their straightforward transformation into a range of β‐amino acid derivatives.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900701