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

2014-07-30
Okumus, Seda
Tanyeli, Cihangir
Demir, Ayhan Sıtkı
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). (C) 2014 Elsevier Ltd. All rights reserved.