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Chiral ferrocenyl ligands with bidentate pyridine donors. Synthesis and application in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropenyl-1-esters

Mroczek, Agnieszka and Erre, Giulia and Taras, Rossana and Gladiali, Serafino Gabriele (2010) Chiral ferrocenyl ligands with bidentate pyridine donors. Synthesis and application in Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenylpropenyl-1-esters. Tetrahedron: Asymmetry, Vol. 21 (15), p. 1921-1927. eISSN 1362-511X. Article.

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DOI: 10.1016/j.tetasy.2010.06.015

Abstract

A synthetic procedure relying on the Friedländer condensation of enantiopure α-amino ferrocenecarboxaldeyde has been devised for the regio-designed elaboration of a pyridine nucleus fused onto the ferrocene scaffold. Three novel bidentate ligands with different pyridine nitrogen donors featuring the [3,2-b]ferrocenopyridine fragment a as the sole chirogenic element have been prepared in enantiopure form through a multi step route involving the diastereoselective deprotonation of a chiral acetal of ferrocenecarboxaldehyde in the stereodetermining step. The ligands were assessed in the Pd-catalyzed allylic alkylation of 1,3-diphenyl-2-propenyl esters with good stereoselectivity.

Item Type:Article
ID Code:5583
Status:Published
Refereed:Yes
Uncontrolled Keywords:Chiral ferrocenyl ligands, alkylation, stereochemistry, catalysis
Subjects:Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Pergamon / Elsevier
eISSN:1362-511X
Copyright Holders:© 2010 Elsevier
Deposited On:11 Mar 2011 12:16

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