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Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions |
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| Authors: | Sergio RossiMaurizio Benaglia Andrea GenoniTiziana Benincori Giuseppe Celentano |
| Institution: | a Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Golgi 19, 24100 Milano, Italy b Dipartimento di Scienze Chimiche ed Ambientali dell’Università dell’Insubria, Via Valleggio, 11, 22100 Como, Italy c Dipartimento di Dipartimento di Scienze Molecolari Applicate ai Biosistemi, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy |
| Abstract: | A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize β-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. |
| Keywords: | Phosphine oxides Organocatalysis Aldol reaction Stereoselection Chirality |
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