Highly diastereoselective aza-aldol reactions of a chiral Ni(II) complex of glycine with imines. An efficient asymmetric approach to 3-perfluoroalkyl-2,3-diamino acids

Autor:	Valery P. Kukhar, Dimitry V Avilov, N Mischenko, Vadim A. Soloshonok, Luc Van Meervelt
Rok vydání:	1997
Předmět:	chemistry.chemical_compound Addition reaction Schiff base Aldol reaction chemistry Organic Chemistry Drug Discovery Glycine Imine Benzophenone Biochemistry Medicinal chemistry
Zdroj:	Tetrahedron Letters. 38:4671-4674
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(97)00963-5
Popis:	The LiCl/base-assisted asymmetric aldol-type addition reaction between the N-(p-methoxyphenyl)imine of trifluoroacetaldehyde and the chiral non-racemic Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone was found to proceed with excellent chemical and stereochemical outcomes allowing for an efficient access to hitherto unknown stereochemically defined β-perfluoroalkyl-α,β-diamino carboxylic acids. A mechanistic rationale for the observed stereochemical preferences is proposed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::32ab24c4c35414f517bd61241d0d43f2 https://doi.org/10.1016/s0040-4039(97)00963-5 Zobrazit plný text záznamu Full Text from ScienceDirect