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Issue 20, 2012
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Another side of the oxazaphospholidine oxide chiral ortho-directing group

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Abstract

A new ferrocenyl oxazaphospholidine oxide 3 was synthesized together with its P-epimer 2 in the reaction of ferrocene lithium with phosphoramidite chloride 1. 3 was successfully derivatized into planar chiral 1,2-ferrocenes, including phosphine ligands, via highly diastereoselective ortho-lithiation and subsequent functionalization; these compounds display opposite planar chirality to those obtained from 2. Some of these 1,2-ferrocenes were further lithiated, allowing for the introduction of a free phosphine group at the oxazaphospholidine ring. The X-ray structures of the compounds 2 and 3 as well as those of the new 1,2-ferrocenes 4 and 7 have been determined.

Graphical abstract: Another side of the oxazaphospholidine oxide chiral ortho-directing group

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Publication details

The article was received on 25 Jan 2012, accepted on 22 Mar 2012, published on 23 Mar 2012 and first published online on 23 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB25187F
Citation: Org. Biomol. Chem., 2012,10, 4036-4042
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    Another side of the oxazaphospholidine oxide chiral ortho-directing group

    N. Martins, N. Mateus, D. Vinci, O. Saidi, A. Brigas, J. Bacsa and J. Xiao, Org. Biomol. Chem., 2012, 10, 4036
    DOI: 10.1039/C2OB25187F

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