New synthetic routes toward enantiopure nitrogen donor ligands

Xavier Sala, Anna M. Rodríguez, Montserrat Rodríguez, Isabel Romero, Teodor Parella, Alexander Von Zelewsky, Antoni Llobet, Jordi Benet-Buchholz

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23 Citations (Scopus)

Abstract

(Chemical Equation Presented) New polypyridylic chiral ligands, having either C3 or lower symmetry, have been prepared via a de novo construction of the pyridine nucleus by means of Kröhnke methodology in the key step. The chiral moieties of these ligands originate from the monoterpen chiral pool, namely (-)-α-pinene ((-)-14, (-)-15) and (-)-myrtenal ((-)-9, (-)-10). Extension of the above-mentioned asymmetric synthesis procedure to the preparation of enantiopure derivatives of some commonly used polypyridylic ligands has been achieved through a new aldehyde building block ((-)-16). As an example, the synthesis of a chiral derivative of N,N-bis(2-pyridylmethyl) ethylamine (bpea) ligand, (-)-19, has been performed to illustrate the viability of the method. The coordinative ability of the ligands has been tested through the synthesis and characterization of complexes [Mn((-)-19)Br2], (-)-20, and [RuCl((-)-10)(bpy)](BF4), (-)-21. Some preliminary results related to the enantioselective catalytic epoxidation of styrene with the ruthenium complex are also presented. © 2006 American Chemical Society.
Original languageEnglish
Pages (from-to)9283-9290
JournalJournal of Organic Chemistry
Volume71
Issue number25
DOIs
Publication statusPublished - 8 Dec 2006

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