Diastereoselective synthesis of N-sulfinyl α-aminophosphine sulfides and phosphines. Issue 23 (7th June 2017)

• Record Type: Journal Article
• Authors: Zhang, Wei; Gilbertson, Scott R.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 23(2017)
• Page Start: 2175
• Page End: 2177
• Publication Date: 2017-06-07
• Subjects: Aminophosphine -- Sulfinyl phosphine -- Phosphine oxide -- Phosphine sulfide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.03.067
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Simple approach to N -sulfinyl α-aminophosphine sulfides and phosphines. Access to chiral ligands from readily available starting materials. A number of potential uses. Transition metal ligands. Nucleolophilic catalysts. Amino acid surrogates. Abstract: The diastereoselective synthesis of N -sulfinyl α-aminophosphine sulfides and phosphines is reported. These molecules are synthesized by formation of sulfinyl imine followed by diastereoselective addition of a diphenylphosphine sulfide. The product N -sulfinyl α-aminophosphine sulfides can be converted to phosphines through removal of the sulfur by reaction with Raney nickel. Hydrolysis of the sulfinyl group provides an amine that can then be attached to other ligands or structural scaffolds.