Asymmetric synthesis of phosphonotrifluoroalanine derivatives via proline-catalyzed direct enantioselective CC bond formation reactions of NH trifluoroacetimidoyl phosphonate

Autor:	Petro P. Onys’ko, Ivanna P. Yelenich, Yuliya V. Rassukana, Yurii Vlasenko
Rok vydání:	2014
Předmět:	Chemistry Stereochemistry Organic Chemistry Synthon Enantioselective synthesis Bond formation Phosphonate Catalysis Inorganic Chemistry chemistry.chemical_compound Acetone Proline Physical and Theoretical Chemistry Enantiomer
Zdroj:	Tetrahedron: Asymmetry. 25:1234-1238
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2014.07.007
Popis:	Based on enantioselective proline-catalyzed reactions between NH-iminotrifluoroethylphosphonate and acetone, an effective synthetic approach to both enantiomers of α-amino-α-trifluoromethyl-γ-oxobutylphosphonate was developed. The synthetic potential of these novel chiral synthons was illustrated by their cyclocondensation reactions with 4-chlorophenylisocyanate or 2,5-dimethoxytetrahydrofuran to afford the first representatives of phosphorylated 3,4-dihydropyrimidin-2-ones or 3H-pyrrolizines, incorporating pharmacophoric optically active fragments of phosphonotrifluoroalanine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::573bf47e5e1bdb81c76db7dbddb4e2ed https://doi.org/10.1016/j.tetasy.2014.07.007 Zobrazit plný text záznamu Full Text from ScienceDirect