| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346096 | Tetrahedron: Asymmetry | 2012 | 9 Pages |
Starting from (1R,2S,3R)-camphordiamine and (hetero)aromatic imidates and orthoformate, nine new camphor-annelated NH-imidazolines were synthesized. Subsequent N-modification was carried out via methylation, acylation, benzoylation, and sulfonylation. Two regioisomers were usually isolated with the ratios reflecting the structure of the starting NH-imidazoline and the electrophile used. All of the successfully prepared N1- and C2-substituted camphor-annelated imidazolines were applied to the asymmetric version of a Cu(II)-catalyzed Henry reaction. The electronic effects of both N1- and C2-pendants on the chemical and asymmetric outcomes of the nitroaldol reaction have been studied and discussed.
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(1R,2S,6R,7S)-1,10,10-Trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC16H21N3[α]D20=-43.2 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-4-(pyrazin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC15H20N4[α]D20=-34.5 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-4-(pyrimidin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC15H20N4[α]D20=-36.0 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-4-(isoquinolin-1-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC20H23N3[α]D20=-74.9 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-4-phenyl-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC17H22N2[α]D20=-30.0 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-4-(1H-pyrrol-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC15H21N3[α]D20=-13.8 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-4-(thiophen-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC15H20N2S[α]D20=-27.2 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
4,4′-Pyridin-2,6-diylbis[(1R,2S,6R,7S)-1,10,10-trimethyl-3,5-diazatricyclo[5.2.1.02,6]dec-3-ene]C27H37N5[α]D20=-24.4 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-1,10,10-Trimethyl-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC11H18N2[α]D20=-26.6 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5,7,10,10-Tetramethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC17H23N3[α]D20=-11.6 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-1,5,10,10-Tetramethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC17H23N3[α]D20=-48.2 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-Benzyl-7,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H27N3[α]D20=+30.4 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-Benzyl-1,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H27N3[α]D20=-14.0 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-5-Isobutyryl-1,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC20H27N3O[α]D20=-51.0 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1R,2S,6R,7S)-5-Benzoyl-1,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H25N3O[α]D20=-94.4 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-(4-Methoxybenzoyl)-7,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC24H27N3O2[α]D20=+2.0 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-(4-Methoxybenzoyl)-1,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC24H27N3O2[α]D20=-95.2 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-(4-Nitrobenzoyl)-7,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H24N4O3[α]D20=+13.6 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-(4-Nitrobenzoyl)-1,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H24N4O3[α]D20=+30.4 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-(4-Methylbenzenesulfonyl)-7,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H27N3O2S[α]D20=+89.4 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1S,2R,6S,7R)-5-(4-Methoxybenzenesulfonyl)-7,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H27N3O3S[α]D20=+88.0 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1S,2R,6S,7R)-5-(4-Nitrobenzenesulfonyl)-7,10,10-trimethyl-4-(pyridin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC22H24N4O4S[α]D20=+81.2 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1S,2R,6S,7R)-5-(4-Methoxybenzoyl)-7,10,10-trimethyl-4-(pyrazin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H26N4O2[α]D20=+26.0 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-(4-Methoxybenzoyl)-1,10,10-trimethyl-4-(pyrazin-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H26N4O2[α]D20=-114.6 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-(4-Methoxybenzoyl)-7,10,10-trimethyl-4-(isoquinolin-1-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC28H29N3O2[α]D20=+102.4 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-(4-Methoxybenzoyl)-1,10,10-trimethyl-4-(isoqiunolin-1-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC28H29N3O2[α]D20=-116.6 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-(4-Methoxybenzoyl)-7,10,10-trimethyl-4-phenyl-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC25H28N2O2[α]D20=+1.4 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-(4-Methoxybenzoyl)-1,10,10-trimethyl-4-phenyl-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC25H28N2O2[α]D20=-62.8 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
(1S,2R,6S,7R)-5-(4-Methoxybenzoyl)-7,10,10-trimethyl-4-(thiophen-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H26N2O2S[α]D20=+9.4 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,6S,7R)
(1R,2S,6R,7S)-5-(4-Methoxybenzoyl)-1,10,10-trimethyl-4-(thiopehen-2-yl)-3,5-diazatricyclo[5.2.1.02,6]dec-3-eneC23H26N2O2S[α]D20=-75.1 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,6R,7S)
N-{(1R,2S,3R,4S)-1,7,7-Trimethyl-3-[(4-methylbenzenesulfonyl)amino]bicyclo[2.2.1] hept-2-yl}pyridine-2-carboxamideC23H29N3O3S[α]D20=+43.8 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,3R,4S)
N-{(1R,2S,3R,4S)-1,7,7-Trimethyl-3-[(4-methoxybenzenesulfonyl)amino]bicyclo[2.2.1] hept-2-yl}pyridine-2-carboxamideC23H29N3O4S[α]D20=+43.6 (c 0.5, CH2Cl2)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1R,2S,3R,4S)
N-[(1S,2R,3S,4R)-3-(4-Methoxybenzoyl)-4,7,7-trimethylbicyclo[2.2.1]hept-2-yl]pyrazine-2-carboxamideC23H28N4O3[α]D20=-78.6 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,3S,4R)
N-[(1S,2R,3S,4R)-3-(4-Methoxybenzoyl)-4,7,7-trimethylbicyclo[2.2.1]hept-2-yl]thiophene-2-carboxamideC23H28N2O3S[α]D20=-30.0 (c 0.5, MeOH)Source of chirality: (1R)-(+)-camphorAbsolute configuration: (1S,2R,3S,4R)
