| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348299 | Tetrahedron: Asymmetry | 2011 | 6 Pages |
New chiral 2-azanorbornane derivatives were prepared and used as (N,N)-donating ligands in a copper-catalyzed Henry reaction yielding up to 62% ee.
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(−)-(1S,3S,4R)-2-[(S)-1-Phenylethyl]-3-hydroxymethyl-2-azabicyclo[2,2,1]heptaneC15H21NO>95% Ee[α]D20=-4.5 (c 1.12, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,S,R,S) (by chemical correlation)
(−)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-azidemethyl-2-azabicyclo[2,2,1]heptaneC15H20N4>95% Ee[α]D20=-71.3 (c 0.60, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(+)-(1S,3S,4R)-2-[(S)-1-Phenylethyl]-3-azidemethyl-2-azabicyclo[2,2,1]heptaneC15H20N4>95% Ee[α]D20=+34.5 (c 0.58, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,S,R,S) (by chemical correlation)
(−)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-aminemethyl-2-azabicyclo[2,2,1]heptaneC15H22N2>95% Ee[α]D20=-17.5 (c 0.40, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(−)-(1S,3S,4R)-2-[(S)-1-Phenylethyl]-3-aminemethyl-2-azabicyclo[2,2,1]heptaneC15H22N2>95% Ee[α]D20=-19.8 (c 0.61, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,S,R,S) (by chemical correlation)
(+)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-(benzylamine)methyl-2-azabicyclo[2,2,1]heptaneC22H28N2>95% Ee[α]D20=+15.7 (c 0.60, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(+)-(1S,3S,4R)-2-[(S)-1-Phenylethyl]-3-(benzylamine)methyl-2-azabicyclo[2,2,1]heptaneC22H28N2>95% Ee[α]D20=+24.0 (c 1.00, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,S,R,S) (by chemical correlation)
(−)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-[(4-chlorophenyl)methylamine]methyl-2-azabicyclo[2,2,1]heptaneC22H27N2Cl>95% Ee[α]D20=-8.5 (c 1.36, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(−)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-[(4-fluorophenyl)methylamine]methyl-2-azabicyclo[2,2,1]heptaneC22H27N2F>95% Ee[α]D20=-16.0 (c 0.75, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(−)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-[(2-naphthyl)methylamine]methyl-2-azabicyclo[2,2,1]heptaneC26H30N2>95% Ee[α]D20=-8.3 (c 0.36, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(−)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-[(9-anthryl)methylamine]methyl-2-azabicyclo[2,2,1]heptaneC30H32N2>95% Ee[α]D20=-22.0 (c 1.10, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
(+)-(1S,3R,4R)-2-[(S)-1-Phenylethyl]-3-(N,N-dimethylamine)methyl-2-azabicyclo[2,2,1]heptaneC17H26N2>95% Ee[α]D20=+25.0 (c 0.24, CH2Cl2)Source of chirality: chiral substrateAbsolute configuration: (S,R,R,S) (by chemical correlation)
