| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347616 | Tetrahedron: Asymmetry | 2008 | 6 Pages |
An efficient bifunctional thiourea catalyzed addition–cyclization reaction of 2-naphthol with α,α-dicyanoolefins is realized under mild conditions to afford the corresponding naphthopyran derivatives in high yields and moderate enantioselectivities. Additionally, the development of an asymmetric three-component one-pot procedure for the synthesis of naphthopyran derivatives is also reported.
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(S)-3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrileC20H14N2OEe = 68%[α]D23.8=-5.2 (c 1.15, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(4-bromophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13BrN2OEe = 71%[α]D27.7=-57.3 (c 0.93, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13ClN2OEe = 84%[α]D24.8=-43.9 (c 0.7, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(4-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13FN2OEe = 90%[α]D27.1=-2.8 (c 0.64, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-p-tolyl-1H-benzo[f]chromene-2-carbonitrileC21H16N2OEe = 79%[α]D24.3=-20.3 (c 3.05, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(4-nitrophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13N3O3Ee = 65%[α]D27.4=-115.9 (c 0.4, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(4-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrileC21H16N2O2Ee = 62%[α]D27.1=-19.5 (c 0.65, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(2,4-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13Cl2N2OEe = 56%[α]D26.8=+4.3 (c 0.73, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3Amino-1-(3-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13FN2OEe = 70%[α]D27.5=-21.7 (c 0.62, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(3-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrileC21H16N2O2Ee = 76%[α]D27.3=-6.6 (c 0.77, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(2-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13ClN2OEe = 67%[α]D23.9=+28.5 (c 0.48, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(3-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrileC20H13ClN2OEe = 65%[α]D25.0=-18.4 (c 0.62, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(furan-2-yl)-1H-benzo[f]chromene-2-carbonitrileC18H12N2O2Ee = 61%[α]D27.3=-45.5 (c 0.41, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-pentyl-1H-benzo[f]chromene-2-carbonitrileC19H20N2OEe = 57%[α]D27.8=+5.5 (c 0.64, CDCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-3-Amino-1-(4-fluorophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrileC21H15FN2O2Ee = 66%[α]D24.6=-51.35 (c 0.54, DMSO)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-Ethyl 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carboxylateC22H18ClNO2Ee = 34%[α]D12.7=+2.5 (c 0.33, CDCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
