The alpha-alkylation of aldehydes is an important transformation. It was and in some way it is still considered the " Holy Grail" of organocatalysis. However, it is still not possible to introduce methyl groups by using methyl iodide as electrophile in a stereoselective organocatalytic promoted alkylation of aldehydes or ketones. The stabilization of carbenium ion by sulfur allowed us to introduce a quite straightforward methodology for a formal a-methylation of aldehydes. The commercially available benzodithiolylium tetrafluoborate is a stable carbenium ion with a rich chemistry and interesting properties. Furthermore, it can be easily removed by nickel Raney or it can be oxidized to the corresponding carbonyl group.

A practical and enantioselective organocatalytic alkylation with benzodithiolylium tetrafluoroborate / A. Gualandi; L. Mengozzi; P. G. Cozzi. - In: CHIMICA OGGI-CHEMISTRY TODAY. - ISSN 0392-839X. - STAMPA. - 32:(2014), pp. 14-17.

A practical and enantioselective organocatalytic alkylation with benzodithiolylium tetrafluoroborate

GUALANDI, ANDREA;MENGOZZI, LUCA;COZZI, PIER GIORGIO
2014

Abstract

The alpha-alkylation of aldehydes is an important transformation. It was and in some way it is still considered the " Holy Grail" of organocatalysis. However, it is still not possible to introduce methyl groups by using methyl iodide as electrophile in a stereoselective organocatalytic promoted alkylation of aldehydes or ketones. The stabilization of carbenium ion by sulfur allowed us to introduce a quite straightforward methodology for a formal a-methylation of aldehydes. The commercially available benzodithiolylium tetrafluoborate is a stable carbenium ion with a rich chemistry and interesting properties. Furthermore, it can be easily removed by nickel Raney or it can be oxidized to the corresponding carbonyl group.
2014
A practical and enantioselective organocatalytic alkylation with benzodithiolylium tetrafluoroborate / A. Gualandi; L. Mengozzi; P. G. Cozzi. - In: CHIMICA OGGI-CHEMISTRY TODAY. - ISSN 0392-839X. - STAMPA. - 32:(2014), pp. 14-17.
A. Gualandi; L. Mengozzi; P. G. Cozzi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/331716
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