The synthesis of enantiomerically pure C2-symmetric bis-pyridinium salts was realized through a simple condensation of 2-pyridyl-carboxyaldehydes with a chiral diamine. The catalytic properties of such novel compounds were preliminarily studied and the trifluoracetate salts of chiral bis-imines of 2-picolinaldehydes derived from 1,1-binaphthyl-2,2-diamine were shown to catalyze the Diels-Alder reaction between cyclopentadiene and ,-unsaturated aldehydes. Modest exo stereoselectivities and enantioselectivities of up to 55% were obtained.
Chiral Bis-pyridinium Salts as Novel Stereoselective Catalysts for the Metal-Free Diels–Alder Cycloaddition of a,b-Unsaturated Aldehydes / A. Genoni, M. Benaglia, A. Puglisi, S. Rossi. - In: SYNTHESIS. - ISSN 0039-7881. - 2011:12(2011), pp. 1926-1929.
|Titolo:||Chiral Bis-pyridinium Salts as Novel Stereoselective Catalysts for the Metal-Free Diels–Alder Cycloaddition of a,b-Unsaturated Aldehydes|
GENONI, ANDREA (Primo)
BENAGLIA, MAURIZIO (Secondo)
PUGLISI, ALESSANDRA (Penultimo)
ROSSI, SERGIO (Ultimo)
|Parole Chiave:||chiral imines; Diels-Alder reaction; enantioselective catalysis; hydrogen bonding activation; pyridinium salt|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2011|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1055/s-0030-1260462|
|Appare nelle tipologie:||01 - Articolo su periodico|