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Asymmetric aldol addition of alpha-azido ketones to ethyl pyruvate mediated by a cinchona-based bifunctional urea catalyst
Date
2014-07-30
Author
Okumus, Seda
Tanyeli, Cihangir
Demir, Ayhan Sıtkı
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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The first asymmetric synthesis of ethyl 4-aryl-3-azido-2-hydroxy-2-methyl-4-oxobutanoates via a cinchona organocatalyst induced aldol addition of alpha-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).
Subject Keywords
Organic Chemistry
,
Biochemistry
,
Drug Discovery
URI
https://hdl.handle.net/11511/47300
Journal
TETRAHEDRON LETTERS
DOI
https://doi.org/10.1016/j.tetlet.2014.06.018
Collections
Department of Chemistry, Article