| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344953 | Tetrahedron: Asymmetry | 2008 | 6 Pages |
N-Nitrosation of (E)-(S)-2-(benzylidene-amino)ethanols 2 with nitric oxide occurred highly diastereoselectively, to give the (2S,4S)-diastereomer dominant N-nitroso-(2S,4S)-1,3-oxazolidines in good yield. Intermediate 2 was prepared from the reaction of benzaldehyde 1 with (S)-2-aminoethanol.
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(2S,4S)-4-Benzyl-3-nitroso-2-phenyloxazolidineC16H16N2O2[α]D20=-45 (c 0.85, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-4-Benzyl-2-(4-chlorophenyl)-3-nitrosooxazolidineC16H15N2O2Cl[α]D20=-49 (c 0.90, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-4-Benzyl-2-(2-chlorophenyl)-3-nitrosooxazolidineC16H15N2O2Cl[α]D20=-48 (c 1.00, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-4-Benzyl-2-(4-nitrophenyl)-3-nitrosooxazolidineC16H15N3O4[α]D20=-52 (c 1.00, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-4-Benzyl-2-(4-methoxyphenyl)-3-nitrosooxazolidineC17H18N2O3[α]D20=-43 (c 1.00, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-4-Benzyl-2-(2-methoxyphenyl)-3-nitrosooxazolidineC17H18N2O3[α]D20=-40 (c 1.20, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-4-Benzyl-3-nitroso-2-p-tolyloxazolidineC17H18N2O2[α]D20=-38 (c 1.00, CHCl3)Source of chirality: l-phenylalanine
(2S,4S)-3-Nitroso-2,4-diphenyloxazolidineC15H14N2O2[α]D20=-35 (c 0.40, CHCl3)Source of chirality: l-(+)-2-phenylglycine
(2S,4S)-2-(4-Chlorophenyl)-3-nitroso-4-phenyloxazolidineC15H13N2O2Cl[α]D20=-37 (c 0.50, CHCl3)Source of chirality: l-(+)-2-phenylglycine
(2S,4S)-2-(2-Chlorophenyl)-3-nitroso-4-phenyloxazolidineC15H13N2O2Cl[α]D20=-32 (c 0.70, CHCl3)Source of chirality: l-(+)-2-phenylglycine
(2S,4S)-2-(4-Nitrophenyl)-3-nitroso-4-phenyloxazolidineC15H13N3O4[α]D20=-39 (c 1.20, CHCl3)Source of chirality: l-(+)-2-phenylglycine
(2S,4S)-2-(4-Methoxyphenyl)-3-nitroso-4-phenyloxazolidineC16H16N2O3[α]D20=-41 (c 1.10, CHCl3)Source of chirality: l-(+)-2-phenylglycine
(2S,4S)-2-(2-Methoxyphenyl)-3-nitroso-4-phenyloxazolidineC16H16N2O3[α]D20=-39 (c 1.00, CHCl3)Source of chirality: l-(+)-2-phenylglycine
(2S,4S)-3-Nitroso-4-phenyl-2-p-tolyloxazolidineC16H16N2O2[α]D20=-32 (c 0.90, CHCl3)Source of chirality: l-(+)-2-phenylglycine
