Asymmetric synthesis of chiral β-hydroxy-α-amino acid derivatives by organocatalytic aldol reactions of isocyanoesters with β,γ-unsaturated α-ketoesters

Autor:	Yan-Qiu Deng, Gui Lu, Ning Lin, Qian Wang, Zhen-Wei Zhang
Rok vydání:	2014
Předmět:	biology Chemistry Organic Chemistry Enantioselective synthesis Cinchona biology.organism_classification Catalysis Inorganic Chemistry chemistry.chemical_compound Hydrolysis Thiourea Aldol reaction Organic chemistry Physical and Theoretical Chemistry Enantiomer Bifunctional
Zdroj:	Tetrahedron: Asymmetry. 25:650-657
ISSN:	0957-4166
Popis:	The first organocatalytic asymmetric aldol reaction of isocyanoesters with various β,γ-unsaturated α-ketoesters has been described. Using cinchona alkaloid-derived bifunctional thiourea as the catalyst, chiral β-hydroxy-α-amino acid derivatives can be obtained in excellent yields and enantioselectivities (up to 95% yield and 92% ee) after acidic hydrolysis. This protocol provides a straightforward method to access multiple substituted β-hydroxy-α-amino acid derivatives with high enantiomeric purity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ccbb1974329836e599dd0bb740a95004 https://doi.org/10.1016/j.tetasy.2014.03.014 Zobrazit plný text záznamu Full Text from ScienceDirect