Add time:07/15/2019         Source:sciencedirect.com

P-Stereogenic oxazaphosphorine compounds of the form 4 have not previously been reported as asymmetric ligands for metal-catalyzed reactions. In an effort to explore the behavior of such oxazaphosphorine ligands, monomeric oxazaphosphorine borane 9 and dimeric oxazaphosphorine boranes 25 and 26 were synthesized as catalyst precursors. The absolute configuration of the phosphorus center contained in the oxazaphosphorines was determined by X-ray crystallography. Rhodium-catalyzed hydrogenation of methyl 2-acetamidoacrylate using a dimerized spiro oxazaphosphorine ligand was performed with up to 15% ee. The extreme sensitivity of the oxazaphosphorine ligands toward oxidation prevented further optimization of the enantioselectivity.

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