The synthesis of a [2.2]paracyclophane-derived secondary phosphine oxide and a study of its reactivity |
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| Authors: | Maulik N. Mungalpara Jingjing Wang Martyn P. Coles Paul G. Plieger Gareth J. Rowlands |
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| Affiliation: | 1. Institute of Fundamental Sciences, Massey University, Private Bag 11 222, Palmerston North, New Zealand;2. School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington, New Zealand |
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| Abstract: | A planar chiral secondary phosphine oxide based on [2.2]paracyclophane was synthesized and its chemistry investigated; it was shown to be a competent pre-ligand in palladium(0)-mediated reactions, and displayed promising activity in gold(I)-catalysed cyclisations. The secondary phosphine oxide could be transformed into a collection of P-stereogenic tertiary phosphine oxides. These are rare examples of the planar chirality of [2.2]paracyclophane being combined with a P-stereogenic centre. Unfortunately, epimerisation of the phosphorus stereocentre during reduction limits the use of this chemistry. |
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| Keywords: | Paracyclophane Secondary phosphine oxide P-stereogenic phosphines Palladium catalysis Gold catalysis |
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