Optically pure N,N- and N,N,N-ligands containing two aziridine rings have been prepared by a three-step sequence. Reactionof optically pure 1,2-aminoalcohols, e.g. (S)-valinol, with 0.5 molar equivalents of dialdehydes, e.g. 1,1’-ferrocene- and 2,6-pyridinedicarboxaldehyde, gave the corresponding diimines, which underwent reduction or addition of organometallic reagents to give 1,2-aminoalcohols with high diastereoselectivities. The aziridine ring was then constructed from the 1,2-aminoalcohol moiety. The new ligands feature two aziridine rings which are connected by a spacer, e.g. ferrocene, or a pyridine ring providing an additional basic center, so that they can act as di- and tridentate ligands towards organometallic species and catalysts, which are active in enantioselective transformations, e.g. Pd-catalyzed allylic alkylation.

Synthesis of Di- and Tridentate Ligands Containing Two Aziridine Rings / C. Fiorelli; D. Savoia; A. Gualandi. - STAMPA. - (2005), pp. P-350-P-350. (Intervento presentato al convegno 13th IUPAC INTERNATIONAL SYMPOSIUM ON ORGANOMETALLIC CHEMISTRY DIRECTED TOWARDS ORGANIC SYNTHESIS tenutosi a GENEVA nel 17-21 LUGLIO 2005).

Synthesis of Di- and Tridentate Ligands Containing Two Aziridine Rings

FIORELLI, CLAUDIO;SAVOIA, DIEGO;GUALANDI, ANDREA
2005

Abstract

Optically pure N,N- and N,N,N-ligands containing two aziridine rings have been prepared by a three-step sequence. Reactionof optically pure 1,2-aminoalcohols, e.g. (S)-valinol, with 0.5 molar equivalents of dialdehydes, e.g. 1,1’-ferrocene- and 2,6-pyridinedicarboxaldehyde, gave the corresponding diimines, which underwent reduction or addition of organometallic reagents to give 1,2-aminoalcohols with high diastereoselectivities. The aziridine ring was then constructed from the 1,2-aminoalcohol moiety. The new ligands feature two aziridine rings which are connected by a spacer, e.g. ferrocene, or a pyridine ring providing an additional basic center, so that they can act as di- and tridentate ligands towards organometallic species and catalysts, which are active in enantioselective transformations, e.g. Pd-catalyzed allylic alkylation.
2005
Book of Abstracts
P-350
P-350
Synthesis of Di- and Tridentate Ligands Containing Two Aziridine Rings / C. Fiorelli; D. Savoia; A. Gualandi. - STAMPA. - (2005), pp. P-350-P-350. (Intervento presentato al convegno 13th IUPAC INTERNATIONAL SYMPOSIUM ON ORGANOMETALLIC CHEMISTRY DIRECTED TOWARDS ORGANIC SYNTHESIS tenutosi a GENEVA nel 17-21 LUGLIO 2005).
C. Fiorelli; D. Savoia; A. Gualandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/9275
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