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 | |
Autori: | 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 | |
Rivista: | ||
Tipologia: | Article (author) | |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1055/s-0030-1260462 | |
Appare nelle tipologie: | 01 - Articolo su periodico |
File in questo prodotto:
File | Descrizione | Tipologia | Licenza | |
---|---|---|---|---|
Synthesis_2011_1926.pdf | Publisher's version/PDF | Open Access Visualizza/Apri |