| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345355 | Tetrahedron: Asymmetry | 2014 | 11 Pages |
The reaction of N-tert-butylsulfinyl imines with nitromethane or nitroethane in the presence of NaHCO3 under solvent-free reaction conditions gave β-nitro amine derivatives with reasonable levels of diastereoselectivity. Enantioenriched N-tert-butylsulfinyl protected α-amino acids or α-amino ketones are accessible upon oxidation of the adducts derived from nitromethane or nitroethane, respectively.
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(R,RS)-N-(tert-Butylsulfinyl)-1-nitrodecan-2-amineC14H30N2O3SEe >95% (NMR)[α]D20=-33 (c 1.21, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesis
(R,RS)-N-(tert-Butylsulfinyl)-3-methyl-1-nitrobutan-2-amineC9H20N2O3SEe >95% (NMR)[α]D20=-61 (c 1.23, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-1-nitro-4-phenylbutan-2-amineC14H22N2O3SEe >95% (NMR)[α]D20=-24 (c 1.14, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(S,SS)-N-(tert-Butylsulfinyl)-2-nitro-1-phenylethanamineC12H18N2O3SEe >95% (NMR)[α]D20=+94 (c 0.44, CH2Cl2)Source of chirality commercially available (S)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (S,SS)
(S,RS)-N-(tert-Butylsulfinyl)-1-(2-benzofuryl)-2-nitroethanamineC14H18N2O4SEe >95% (NMR)[α]D20=61.9 (c 1.66, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(S,RS)-N-(tert-Butylsulfinyl)-1-(2-benzofuryl)-2-nitroethanamineC9H20N2O3SEe >95% (NMR)[α]D20=-89 (c 1.24, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-2-methyl-1-nitroheptan-2-amineC12H26N2O3SEe >95% (NMR)[α]D20=-52.3 (c 1.28, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-2-aminodecanoic acidC14H29NO3SEe >95% (NMR)[α]D20=-20.2 (c 2.26, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(S,SS)-N-(tert-Butylsulfinyl)-2-amino-3-methylbutanoic acidC9H19NO3SEe >95% (NMR)[α]D20=+84.2 (c 1.07, CH2Cl2)Source of chirality commercially available (S)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (S,SS)
(R,RS)-N-(tert-Butylsulfinyl)-2-amino-4-phenylbutanoic acidC14H21NO3SEe >95% (NMR)[α]D20=-19.8 (c 1.00, CHCl3)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-2-amino-2-methylbutanoic acidC9H19NO3SEe >95% (NMR)[α]D20=-70.1 (c 0.79, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-2-amino-2-methylheptanoic acidC12H25NO3SEe >95% (NMR)[α]D20=-20.6 (c 1.77, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(S,SS)-N1-(Benzyloxycarbonyl)-N2-(tert-butylsulfinyl)-3-methylbutane-1,2-diamineC17H28N2O3SEe >95% (NMR)[α]D20=+56 (c 1.04, CH2Cl2)Source of chirality commercially available (S)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (S,SS)
(R,RS)-N-(tert-Butylsulfinyl)-3-aminoundecan-2-oneC15H31NO2SEe >95% (NMR)[α]D20=-146 (c 1.07, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-3-amino-4-methylpentan-2-oneC10H21NO2SEe >95% (NMR)[α]D20=-136 (c 0.23, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-3-amino-5-phenylpentan-2-oneC15H23NO2SEe >95% (NMR)[α]D20=-99.2 (c 1.00, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-3-amino-5-methylhexan-2-oneC11H23NO2SEe >95% (NMR)[α]D20=-168.5 (c 0.79, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
(R,RS)-N-(tert-Butylsulfinyl)-3-amino-4-phenylbutan-2-oneC14H21NO2SEe >95% (NMR)[α]D20=-122 (c 1.04, CH2Cl2)Source of chirality commercially available (R)-tert-butanesulfinamide and diastereoselective synthesisAbsolute configuration: (R,RS)
