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.
Chiral Bis-pyridinium Salts as Novel Stereoselective Catalysts for the Metal-Free Diels–Alder Cycloaddition of a,b-Unsaturated Aldehydes
A. GenoniPrimo
;M. BenagliaSecondo
;A. PuglisiPenultimo
;S. RossiUltimo
2011
Abstract
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.File | Dimensione | Formato | |
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