ChemInform Abstract: General Syntheses of Optically Active α‐Trifluoromethylated Amines via Ring‐Opening Reactions of N‐Benzyl‐2‐trifluoromethylaziridine.

Abstract

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Discovery of Tetrasubstituted Imidazolines as Potent and Selective Neuropeptide Y Y5 Receptor Antagonists: Reduced Human Ether-a-go-go Related Gene Potassium Channel Binding Affinity and Potent Antiobesity Effect

“…The aminoalcohol intermediates 11a-f having bis(4-fluorophenyl) or bis(6-fluoro-3-pyridyl) groups were prepared from esters 5, 15a 6, 7, 15b 8, 15c and 9 15d (Scheme 1). Esters 5-8 were converted to 10a-d by coupling with 4-fluorophenylmagnesium bromide, followed by provided the corresponding aziridines 12a-f. 16 The aziridine ring was opened using sodium azide to give 13a-f, 17 which were reduced by hydrogenation to give diamines 14a-f. 18 Formation of the imidazoline rings of 1c-f, 1g′, and 1h-i was accomplished using reaction conditions d 19 or e, 20 and 21a). The stereochemistry of the 1-position of 18 and 21a was supported by nuclear Overhauser effect (NOE) studies of the corresponding morpholinone and piperazinone derivatives 23 and 24, as shown in Figure 2.…”

“…Synthesis of the imidazoline derivatives 1c − i from aminoalcohols 11a − f is shown in Scheme . Treatment of the aminoalcohols 11a − f with triphenylphosphine and bromine provided the corresponding aziridines 12a − f . The aziridine ring was opened using sodium azide to give 13a − f , which were reduced by hydrogenation to give diamines 14a − f .…”

Organocatalytic Asymmetric Reduction of Fluorinated Alkynyl Ketimines

“…3 For example, in 2009, Shibata reported the enantioselective trifluoromethylation of imine with Me 3 SiCF 3 by employing Cinchona alkaloids as chiral catalysts. 3h The other process is the asymmetric transformation of the fluorinated block, 4 such as nucleophilic additions to fluorinated imines, 5 isomerization of fluorinated imines, 6 ring opening reaction of active trifluomethylated epoxides, 7 and kinetic resolution of racemic trifluoromethyl amines. 8 It is noteworthy that asymmetric hydrogenation of fluorinated imines/enamides is regarded as one of the most straightforward and atom-economic methods toward the synthesis of chiral trifluoromethylated amines.…”