Chemoselective opening of Vince lactam epoxide with nitrogen nucleophiles

Autor:	Fabio Ponticelli, Luca Guideri, Gianluca Giorgi
Rok vydání:	2011
Předmět:	Nucleophilic addition Hydrogen bond Stereochemistry Organic Chemistry Epoxide Biochemistry chemistry.chemical_compound chemistry Nucleophile Drug Discovery Peptide bond Chemoselectivity Vince lactam Derivative (chemistry)
Zdroj:	Tetrahedron. 67:1463-1467
ISSN:	0040-4020
DOI:	10.1016/j.tet.2010.12.031
Popis:	Here is reported the chemoselective opening of the amide bond on a Vince lactam derivative with amines, without the cleavage of the epoxide-moiety, getting five new epoxides. Also reported is the rearrangement of the epoxides into the respective five new oxazolidinones with the use of BF3·Et2O. Crystal structures of some molecules and hydrogen bonding interactions are discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::259002f0b03f3bf67832569ff304c20e https://doi.org/10.1016/j.tet.2010.12.031 Zobrazit plný text záznamu Full Text from ScienceDirect