The straightforward synthesis of a series of enantiomerically pure pyridine- and quinoline-N-oxides and their use as new organocatalysts for the enantioselective allylation of arom. aldehydes with allyl(trichloro)silane is reported. The catalysts were readily assembled by combining com. available enantiopure diamines with heterocyclic carboxylic acid N-oxides. The obtained compds. showed moderate to good chem. efficiency (up to 73% chem. yield) and satisfactory stereoselectivity (up to 50% ee). Tentative models of stereoselection were proposed to account for the stereochem. outcome of the reaction and to explain how the structural features of the catalyst control the stereoselectivity.

Readily available pyridine- and quinoline-N-oxides as new organocatalysts for the enantioselective allylation of aromatic aldehydes with allyl(trichloro)silane / L. Pignataro, M. Benaglia, M. Cinquini, F. Cozzi, G. Celentano. - In: CHIRALITY. - ISSN 0899-0042. - 17:7(2005), pp. 396-403.

Readily available pyridine- and quinoline-N-oxides as new organocatalysts for the enantioselective allylation of aromatic aldehydes with allyl(trichloro)silane

L. Pignataro;M. Benaglia;M. Cinquini;F. Cozzi;G. Celentano
2005

Abstract

The straightforward synthesis of a series of enantiomerically pure pyridine- and quinoline-N-oxides and their use as new organocatalysts for the enantioselective allylation of arom. aldehydes with allyl(trichloro)silane is reported. The catalysts were readily assembled by combining com. available enantiopure diamines with heterocyclic carboxylic acid N-oxides. The obtained compds. showed moderate to good chem. efficiency (up to 73% chem. yield) and satisfactory stereoselectivity (up to 50% ee). Tentative models of stereoselection were proposed to account for the stereochem. outcome of the reaction and to explain how the structural features of the catalyst control the stereoselectivity.
Enantiomerically pure N-oxides; Organic catalysis; Stereoselective catalysis; Synthesis of homoallylic alcohols
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/7457
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