title: P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis.
abstract: The synthesis of stereodefined β-aminophosphines having both carbon- and phosphorus-based chirality centers is described. The method involves resolution of a mixture of β-aminophosphine oxide diastereomers accessed by ring-opening of an amino alcohol-derived cyclic sulfamidate. A stereospecific, borane-promoted reduction of β-aminophosphine oxides, which occurs under mild conditions and with inversion of configuration at phosphorus, is a key step in this process. The products obtained are new building blocks for the synthesis of P-chiral ligands and organocatalysts. In a proof-of-concept application in organocatalysis, the diastereomeric P-chiral β-aminophosphine-based bifunctional thioureas displayed significantly different activities in the Morita-Baylis-Hillman reaction of methyl acrylate with benzaldehyde derivatives.
authors.affiliation: Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.
authors.forename: Hsin Y
authors.initials: HY
authors.lastname: Su
authors.affiliation: Department of Chemistry, University of Toronto , Toronto, Ontario M5S 3H6, Canada.
authors.forename: Mark S
authors.identifier: 0000-0003-3424-4380
authors.initials: MS
authors.lastname: Taylor