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Issue 3, 2006
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Modular multidentate phosphine ligands: application to palladium-catalyzed allylic alkylations

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Abstract

Multidentate phosphines were readily obtained by reaction of chiral multidentate amines, prepared via ring opening of (S)-N-tosyl-2-isopropylaziridine with ammonia, primary, and secondary amines, with achiral phosphorus containing building blocks. The phosphines were used in palladium-catalyzed alkylation of rac-3-cyclohexenyl and cyclopentenyl carbonates. The enantioselectivity and reactivity were largely dependent on the structure of the amine core of the ligands. Up to 88% ee was observed in reactions with the six-membered substrate.

Graphical abstract: Modular multidentate phosphine ligands: application to palladium-catalyzed allylic alkylations

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Article information


Submitted
30 Sep 2005
Accepted
05 Dec 2005
First published
04 Jan 2006

Org. Biomol. Chem., 2006,4, 544-550
Article type
Paper

Modular multidentate phosphine ligands: application to palladium-catalyzed allylic alkylations

Y. Pei, E. Brulé and C. Moberg, Org. Biomol. Chem., 2006, 4, 544
DOI: 10.1039/B513906F

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