Novel O-ferrocenoyl hydroxyproline conjugates: Synthesis, characterization and catalytic properties

Autor:	Lo’ay Al-Momani, Anas Lataifeh
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Stereochemistry Catalysis Amino acid Inorganic Chemistry Hydroxyproline chemistry.chemical_compound Residue (chemistry) chemistry Aldol reaction Ferrocene Materials Chemistry Amine gas treating Proline Physical and Theoretical Chemistry
Zdroj:	Inorganica Chimica Acta. 394:176-183
ISSN:	0020-1693
Popis:	A series of mono- and disubstituted O -ferrocenoyl conjugates of 3- trans - and 4- trans- hydroxy- L -proline amino acids are synthesized. These conjugates are protected by tert- butloxycarbonyl ( Boc ) group at the N -terminus. The Boc removal of the ferrocene (Fc) hydroxy- L -proline conjugates affords a series of mono- and disubstituted Fc conjugates containing free amine at the N -terminus. These conjugates are characterized by NMR and IR spectroscopies as well as mass (MS) spectrometry. The catalytic properties of the free amine Fc conjugates toward aldol addition reaction are studied. The enantioselectivity of the aldol reaction products in acetone solvent is determined by the position of the N -atom in the proline residue with respect to the proline point of attachment to the Fc scaffold. The 4- trans- hydroxy- L -proline containing Fc catalyst favors the production of the R -isomer, while Fc catalysts containing 3- trans- hydroxy- L -proline favors the production of the S -isomer.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2eca597a0d4b2bca16b279150f15ec20 https://doi.org/10.1016/j.ica.2012.07.015 Zobrazit plný text záznamu Full Text from ScienceDirect