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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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