Asymmetric aldol addition of α-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst

Asymmetric aldol addition of α-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst

The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of α-azido ketones to ethyl pyruvate has been developed. The coupling reaction under optimized conditions was carried out to furnish tetrafunctionalized synt...

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Veröffentlicht in:Tetrahedron letters 2014-07, Vol.55 (31), p.4302-4305
Hauptverfasser: Okumuş, Seda, Tanyeli, Cihangir, Demir, Ayhan S.
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Aldol reaction
Asymmetry
Bifunctional urea
Chemical reactions
Cinchona alkaloids
C–C coupling
Ketones
Pyruvates
Synthesis
Tetrahedrons
Ureas
α-Azido ketone
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Zusammenfassung:The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of α-azido ketones to ethyl pyruvate has been developed. The coupling reaction under optimized conditions was carried out to furnish tetrafunctionalized synthons with enantioselectivities of up to 91:9 and enriched diastereoselectivities of up to 95:5 (syn:anti).
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.06.018