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A number of new chiral diphosphine ligands with a pinene framework were synthesized and tested in some transition metal-catalyzed asymmetric reactions (enantioselectivities up to 84% ee were achieved). The [2,3]-sigmatropic allylphosphinite-allyl phosphine oxide rearrangement was applied as a key step of the synthesis. An improved procedure for the phosphine oxide reduction and a new protocol for...
Bromodiphosphine oxide 3 was obtained from the selectively protected chiral diol 2 by the double [2,3]-sigmatropic shift of an intermediate phosphinite. The bromophosphine oxide derivative 3 was converted by radical cyclisation into rigid bicyclic diphosphine 1. The diphosphine 1 was characterised and tested as a ligand in several metal catalytic reactions.
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