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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

Author:
Concellón Gracia, José ManuelUniovi authority; Rodríguez Solla, HumbertoUniovi authority; Simal Fernández, CarmenUniovi authority; Amo Sánchez, Vicente delUniovi authority; García-Granda, SantiagoUniovi authority; Díaz Fernández, María del RosarioUniovi authority
Subject:

Addition To Carbonyl Compounds; Enolates; Imines; Mannich Reaction; Samarium

Publication date:
2009
Publisher version:
http://dx.doi.org/10.1002/adsc.200900534
Citación:
Advanced Synthesis & Catalysis, 351(17), p. 2991–3000 (2009); doi:10.1002/adsc.200900534
Descripción física:
p. 2991-3000
Abstract:

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.

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.

URI:
http://hdl.handle.net/10651/10031
ISSN:
1615-4150
Identificador local:

20090192

DOI:
10.1002/adsc.200900534
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