title: Organic base-catalyzed stereodivergent synthesis of (R)- and (S)-3-amino-4,4,4-trifluorobutanoic acids.
abstract: Organic base-catalyzed reaction of (S)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine with dialkyl malonates was found to be effective for synthesis of both (S,S(S)) and (R,S(S)) β-aminomalonates in high yield with good to excellent diastereoselectivity (76-98% de). The products of this Mannich reaction provide direct access to β-trifluoromethyl-β-alanine of either (R) or (S) absolute configuration.
authors.affiliation: Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan. nozshiba@nitech.ac.jp
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
authors.forename: Takayuki
authors.initials: T
authors.lastname: Nishimine
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Shibata
authors.forename: Etsuko
authors.initials: E
authors.lastname: Tokunaga
authors.forename: Kosuke
authors.initials: K
authors.lastname: Kawada
authors.forename: Takumi
authors.initials: T
authors.lastname: Kagawa
authors.forename: Alexander E
authors.initials: AE
authors.lastname: Sorochinsky
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D020148:Butyric Acid / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D013237:Stereoisomerism
chemical_list: D000588:Amines; D020148:Butyric Acid