title: Asymmetric Rh(I)-catalyzed addition of MIDA boronates to N-tert-butanesulfinyl aldimines: development and comparison to trifluoroborates.
abstract: The Rh(I)-catalyzed addition of alkenyl and aryl MIDA boronates to N-tert-butanesulfinyl aromatic and aliphatic imines proceeds in good yields (up to 99%) and with very high selectivity (98:2 to >99:1). In comparison to trifluoroborates, higher yields and selectivities are observed for the addition to N-tert-butanesulfinyl aromatic imines. This new method expands upon the versatility of the Rh(I)-catalyzed addition of boron reagents to imines, thereby further enabling the synthesis of chiral alpha-branched amines.
authors.affiliation: Department of Chemistry, University of California, Berkeley, California 94720, USA.
authors.forename: Katrien
authors.initials: K
authors.lastname: Brak
authors.forename: Jonathan A
authors.initials: JA
authors.lastname: Ellman
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D001881:Borates / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007098:Imino Acids / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000588:Amines; D001881:Borates; D001897:Boronic Acids; D002073:Butanes; D007097:Imines; D007098:Imino Acids; C533766:N-methyliminodiacetic acid; D013452:Sulfonium Compounds; D012238:Rhodium; C098759:fluoroboric acid