The Addition Reaction of Samarium Enolates and 2-Haloenolates Derived from Esters, and Amides to Imines. Totally Stereoselective Synthesis of Enantiopure 3,4-Diamino Esters or Amides

The addition reaction of samarium enolates and 2‐haloenolates derived from esters and amides to imines takes place in an efficient manner. A novel protocol to perform the addition reaction of samarium enolates derived from esters or amides to chiral 2‐aminoimines, with total stereoselectivity and wi...

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Veröffentlicht in:Advanced synthesis & catalysis 2009-11, Vol.351 (17), p.2991-3000
Hauptverfasser: Concellón, José M., Rodríguez-Solla, Humberto, Simal, Carmen, del Amo, Vicente, García-Granda, Santiago, Díaz, M. Rosario
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Sprache:eng
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Zusammenfassung:The addition reaction of samarium enolates and 2‐haloenolates derived from esters and amides to imines takes place in an efficient manner. A novel protocol to perform the addition reaction of samarium enolates derived from esters or amides to chiral 2‐aminoimines, with total stereoselectivity and without racemization, is also reported. The use of samarium enolates in place of other classic metallic enolates (lithium, magnesium, etc.) could be a valuable alternative to obtain enantiopure 3,4‐diamino esters or amides, when enolates of low basicity are necessary.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900534