First Catalytic Asymmetric Synthesis of β‐Amino‐β‐polyfluoroalkyl Ketones via Proline‐Catalyzed Direct Asymmetric Carbon—Carbon Bond Formation Reaction of Polyfluoroalkylated Aldimines.

Abstract

Amines Q 0120First Catalytic Asymmetric Synthesis of β-Amino-β-polyfluoroalkyl Ketones via Proline-Catalyzed Direct Asymmetric Carbon-Carbon Bond Formation Reaction of Polyfluoroalkylated Aldimines. -This asymmetric C-C bond forming reaction gives moderate yields but proceeds with high enantioselectivity. -(FUNABIKI*, K.; NAGAMORI, M.; GOUSHI, S.; MATSUI, M.; Chem. Commun.

Chiral N‐Phosphonyl Imine Chemistry: Asymmetric Synthesis of α‐Alkyl β‐Amino Ketones by Reacting Phosphonyl Imines with Ketone‐Derived Enolates

“…Flash column chromatography was performed using silica gel (Merck 60, 230-400 mesh). NMR spectra were recorded at 500 ⁄ 300, 125 202 MHz for 1 H, 13 C and 31 P, respectively. Internal TMS (d = 0.0 ppm) was used as the reference for 1 H NMR and 13 C NMR.…”

“…So far, several synthetic methods have been developed for the synthesis of enantiomerically pure b-amino ketones, but there has been limited work on asymmetric additions of ketone-derived enolates onto chiral imines. In fact, the asymmetric synthesis of branched b-amino ketone derivatives has not been well documented so far (11)(12)(13)(14)(15)(16)(17)(18)(19). Recently, we established new chiral phosphoramide ⁄ N-phosphonyl imine chemistry (20)(21)(22)(23)(24) and developed an efficient procedure for the asymmetric synthesis of unbranched b-amino ketones (21) and other carbonyl derivatives (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) with good to excellent yields and diastereoselectivity.…”