P-Stereogenic β-Aminophosphines: Preparation and Applications in Enantioselective Organocatalysis.

J Org Chem

Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.

Published: March 2017

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.

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Source
http://dx.doi.org/10.1021/acs.joc.7b00199DOI Listing

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