A library of 16 chiral tropos phosphorus-ligands, based on a chiral P-bound alcohol or secondary amine and a flexible (tropos) P-bound biphenol unit, was synthesised. This ligand library allowed the screening of 16 homocombinations and 115 heterocombinations for the rhodium catalysed asymmetric hydrogenation of methyl N-acetamido acrylate. The screening resulted in the identification of a phosphite/phosphoramidite heterocombination, which proved to be extremely effective and enantioselective (100% yield, 94% ee).
Rh-catalysed asymmetric hydrogenations with a dynamic library of chiral tropos phosphorus-ligands / C. Monti, C. Gennari, U. Piarulli. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 45:37(2004), pp. 6859-6862. [10.1016/j.tetlet.2004.07.100]
Rh-catalysed asymmetric hydrogenations with a dynamic library of chiral tropos phosphorus-ligands
C. MontiPrimo
;C. GennariSecondo
;
2004
Abstract
A library of 16 chiral tropos phosphorus-ligands, based on a chiral P-bound alcohol or secondary amine and a flexible (tropos) P-bound biphenol unit, was synthesised. This ligand library allowed the screening of 16 homocombinations and 115 heterocombinations for the rhodium catalysed asymmetric hydrogenation of methyl N-acetamido acrylate. The screening resulted in the identification of a phosphite/phosphoramidite heterocombination, which proved to be extremely effective and enantioselective (100% yield, 94% ee).
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