Instant ligand libraries. Parallel synthesis of monodentate phosphoramidites and in situ screening in asymmetric hydrogenation.
Chiral phosphoramidites have been identified as excellent ligands for various metal-catalyzed enantioselective transformations. Taking advantage of their easy preparation and modular nature, we designed a fully automated protocol for the parallel preparation of a library of 32 phosphoramidites and its screening in asymmetric hydrogenation of amino acid precursors. This initial study led to the discovery of a new ligand for the preparation of an enantiopure beta(3)-homoalanine precursor. [structure--see text]
Lefort
Laurent
L
DSM Pharma Chemicals-Advanced Synthesis, Catalysis and Development, P.O. Box 18, 6160 MD Geleen, The Netherlands.
Boogers
Jeroen A F
JA
de Vries
André H M
AH
de Vries
Johannes G
JG
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D008024:Ligands; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D000588:Amines; D000596:Amino Acids; D008024:Ligands; D010756:Phosphoric Acids; C011067:phosphoramidic acid