| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348669 | Tetrahedron: Asymmetry | 2006 | 13 Pages |
Asymmetric halomethoxylation of chiral α,β-unsaturated carboxylic acid derivatives was performed with halogens (Br2/I2) promoted by silver(I) salts with high regio- and anti-selectivity and moderate to good diastereoselectivity. Reagent controlled diastereoselectivity was observed for N-cinnamoyl-2-oxazolidinone substrates especially for cinnamoyl and electron-deficient cinnamoyl substrates, when Ag2O was used as a promoter instead of AgNO3. Enoyl substrates containing Oppolzer’s sultam chiral auxiliary are independent of the counter ion of the Ag(I) salt. This method was applied to a short synthesis of both enantiomers of N-protected syn-β-methoxyphenylalanine, and N- and O-protected syn-β-methoxytyrosine, unusual amino acid components of biologically active cyclic peptide and depsipeptide antibiotics.
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anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-methoxy-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H20BrNO4Ee = 100%[α]D27=+84.3 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-methoxy-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H20BrNO4Ee = 100%[α]D27=-4.8 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-methoxy-3′-(2-nitrophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H19BrN2O6Ee = 100%[α]D27=+171.35 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-methoxy-3′-(2-nitrophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H19BrN2O6Ee = 100%[α]D27=+18.6 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-methoxy-3′-(4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC17H22INO5Ee = 100%[α]D27=+22.5 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Iodo-3′-methoxy-3′-(4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC17H22INO5Ee = 100%[α]D27=-19.5 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-methoxy-3′-(3-bromo-4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC21H21Br2NO5Ee = 100%[α]D28=+88.9 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-methoxy-3′-(3-bromo-4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC21H21Br2NO5Ee = 100%[α]D28=+8.4 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-methoxy-3′-(2-chlorophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H19BrClNO4Ee = 100%[α]D27=+77.8 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-methoxy-3′-(2-chlorophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H19BrClNO4Ee = 100%[α]D27=+7.3 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-methoxy-3′-(4-benzyloxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC23H26INO5Ee = 100%[α]D27=+78.9 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Iodo-3′-methoxy-3′-(4-benzyloxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC23H26INO5Ee = 100%[α]D27=+21.8 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-methoxy-3′-(3,4-dimethoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H24INO6Ee = 100%[α]D27=+75.0 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Iodo-3′-methoxy-3′-(3,4-dimethoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H24INO6Ee = 100%[α]D27=-3.85 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-methoxy-3′-(3,4,5-trimethoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC19H26INO7Ee = 100%[α]D27=+86.6 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Iodo-3′-methoxy-3′-(3,4,5-trimethoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC19H26INO7Ee = 100%[α]D27=-17.1 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-methoxy-3′-(2-naphthyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC20H22INO4Ee = 100%[α]D27=+108.6 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Iodo-3′-methoxy-3′-(2-naphthyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC20H22INO4Ee = 100%[α]D27=-39.5 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-(2′-Bromo-3′-methoxy-butionyl)-4-(1-methylethyl)-2-oxazolidinoneC11H18BrNO4Ee = 100%[α]D27=+60.6 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(2R,2′R,3′R)-N-[2′-Iodo-3′-methoxy-3′-phenyl-propionyl]-bornanesultamC20H26INO4SEe = 100%[α]D27=-102.2 (c 1.0, CHCl3)Source of chirality: 2R-bornanesultamAbsolute configuration: (2R,2′R,3′R)
anti-(2R,2′S,3′S)-N-[2′-Iodo-3′-methoxy-3′-phenyl-propionyl]-bornanesultamC20H26INO4SEe = 100%[α]D27=-7.00 (c 1.0, CHCl3)Source of chirality: 2R-bornanesultamAbsolute configuration: (2R,2′S,3′S)
anti-(2R,2′R,3′R)-N-[2′-Bromo-3′-methoxy-3′-(2-nitrophenyl)-propionyl]-bornanesultamC20H25BrN2O6SEe = 100%[α]D27=-109.1 (c 1.0, CHCl3)Source of chirality: 2R-bornanesultamAbsolute configuration: (2R,2′R,3′R)
anti-(2R,2′S,3′S)-N-[2′-Bromo-3′-methoxy-3′-(2-nitrophenyl)-propionyl]-bornanesultamC20H25BrN2O6SEe = 100%[α]D27=+56.2 (c 1.0, CHCl3)Source of chirality: 2R-bornanesultamAbsolute configuration: (2R,2′S,3′S)
anti-(2R,2′R,3′R)-N-[2′-Bromo-3′-methoxy-3′-(4-methoxyphenyl)-propionyl]-bornanesultamC21H28BrNO5SEe = 100%[α]D27=-90.3 (c 1.0, CHCl3)Source of chirality: 2R-bornanesultamAbsolute configuration: (2R,2′R,3′R)
anti-(2R,2′S,3′S)-N-[2′-Bromo-3′-methoxy-3′-(4-methoxyphenyl)-propionyl]-bornanesultamC21H28BrNO5SEe = 100%[α]D27=+19.3 (c 1.0, CHCl3)Source of chirality: 2R-bornanesultamAbsolute configuration: (2R,2′S,3′S)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-ethoxy-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC17H22BrNO4Ee = 100%[α]D27=+0.7 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-ethoxy-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC17H22BrNO4Ee = 100%[α]D27=+94.5 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-(2-methoxy-ethoxy)-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H24BrNO5Ee = 100%[α]D27=+99.8 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-(2-methoxy-ethoxy)-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H24BrNO5Ee = 100%[α]D27=-4.7 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-ethoxy-3′-(2-nitrophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC17H21BrN2O6Ee = 100%[α]D27=+101.4 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-ethoxy-3′-(2-nitrophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC17H21BrN2O6Ee = 100%[α]D27=-92.7 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Bromo-3′-(2-methoxy-ethoxy)-3′-(2-nitrophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H23BrN2O7Ee = 100%[α]D27=+147.3 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Bromo-3′-(2-methoxy-ethoxy)-3′-(2-nitrophenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H23BrN2O7Ee = 100%[α]D27=-89.9 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-ethoxy-3′-(4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC18H24INO5Ee = 100%[α]D27=+89.8 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′S,3′S)-3-[2′-Iodo-3′-(2-methoxy-ethoxy)-3′-(4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC19H26INO6Ee = 100%[α]D27=+86.1 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′S)
anti-(4S,2′R,3′R)-3-[2′-Iodo-3′-(2-methoxy-ethoxy)-3′-(4-methoxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC19H26INO6Ee = 100%[α]D27=-12.95 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′R)
syn-(4S,2′S,3′R)-3-[2′-Azido-3′-methoxy-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H20N4O4Ee = 100%[α]D27=+48.75 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′R)
syn-(4S,2′R,3′S)-3-[2′-Azido-3′-methoxy-3′-phenyl-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC16H20N4O4Ee = 100%[α]D27=+44.3 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′S)
syn-(2S,3R)-2-Azido-3-methoxy-3-phenyl-propionic acidC10H11N3O3Ee = 100%[α]D27=-92.5 (c 1.0, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (2S,3R)
syn-(2R,3S)-2-Azido-3-methoxy-3-phenyl-propionic acidC10H11N3O3Ee = 100%[α]D27=+92.5 (c 1.0, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (2R,3S)
syn-(4S,2′S,3′R)-3-[2′-Azido-3′-methoxy-3′-(4-benzyloxyphenyl)-propionyl]-4-(1-methylethyl)-2-oxazolidinoneC23H26N4O5Ee = 100%[α]D27=+21.5 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′S,3′R)
syn-(4S,2′R,3′S)-3-[2′-Azido-3′-methoxy-3′-(4-benzyloxyphenyl)-propionyl]-4-(1-methylethyl)-2- oxazolidinoneC23H26N4O5Ee = 100%[α]D27=+87.6 (c 1.0, CHCl3)Source of chirality: 4S-(1-methylethyl)-2-oxazolidinoneAbsolute configuration: (4S,2′R,3′S)
syn-(2S,3R)-2-Azido-3-(4-benzyloxyphenyl)-3-methoxy-propionic acidC17H17N3O4Ee = 100%[α]D27=-94.2 (c 1.0, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (2S,3R)
syn-(2R,3S)-2-Azido-3-(4-benzyloxyphenyl)-3-methoxy-propionic acidC17H17N3O4Ee = 100%[α]D27=+94.2 (c 1.0, CHCl3)Source of chirality: Asymmetric synthesisAbsolute configuration: (2R,3S)
