| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350881 | Tetrahedron: Asymmetry | 2005 | 12 Pages |
A short and efficient synthesis of a novel family of quinone-substituted BINOL-type ligands exploiting the chromium-templated [3+2+1]benzannulation reaction as the key step is reported.
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(R)-6,6′-Di(naphthalene-1,4-dione-2-yl)-2,2′-dimethoxy-1,1′-binaphthylC42H26O6Ee >99%[α]D23=-286 (c 0.048, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-6,6′-Di(naphthalene-1,4-dione-2-yl)-2,2′-diethoxy-1,1′-binaphthylC44H30O6Ee >99%[α]D23=-265 (c 0.022, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-6,6′-Di(naphthalene-1,4-dione-2-yl)-2,2′-dihydroxy-1,1′-binaphthylC40H22O6Ee >99%[α]D23=-310 (c 0.06, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Diodo-2,2′-diethoxy-1,1′-binaphthylC24H20I2O2Ee >99%[α]D23=-78 (c 0.35, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Di[(trimethylsilyl)ethynyl]-2,2′-diethoxy-1,1′-binaphthylC34H38O2Si2Ee >99%[α]D23=-50 (c 0.36, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Diethynyl-2,2′-diethoxy-1,1′-binaphthylC28H22O2Ee >99%[α]D23=-7.5 (c 0.39, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Di(naphthalene-1,4-dione-2-yl)-2,2′-diethoxy-1,1′-binaphthylC44H30O6Ee >99%[α]D23=-110 (c 0.05, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Di(naphthalene-1,4-dione-2-yl)-2,2′-diol-1,1′-binaphthylC44H22O6Ee >99%[α]D23=+63 (c 0.15, THF)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Diiodo-2,2′-methylenedioxy-1,1′-binaphthylC21H12I2O2Ee >99%[α]D23=-542 (c 0.35, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Di[(trimethylsilyl)ethynyl]-2,2′-methylenedioxy-1,1′-binaphthylC31H30O2Si2Ee >99%[α]D23=-729 (c 0.28, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Diethynyl-2,2′-methylenedioxy-1,1′-binaphthylC25H14O2Ee >99%[α]D23=-769 (c 0.4, CHCl3)Source of chirality:(R)-1,1′-bi-2-naphthylAbsolute configuration:R
(R)-3,3′-Di(naphthalene-1,4-dione-2-yl)-2,2′-methylenedioxy-1,1′-binaphthylC41H22O6Ee >99%[α]D23=-158 (c 0.36, CHCl3)Source of chirality: (R)-1,1′-bi-2-naphthylAbsolute configuration: R
(R)-3,3′-Di(2-naphthalene-1,4-dimethoxy)-2,2′-methylenedioxy-1,1′-binaphthylC45H34O6Ee >99%[α]D23=-184 (c 0.2, CHCl3)Source of chirality: (R)-1,1′-bi-2-naphthylAbsolute configuration: R
(−)-2,2′,3,3′-Tetraethyl-8,8′-dimethoxy-7,7′-bis(phenanthrene-1,4-dione)C38H34O6Ee >99%[α]D23=-10 (c 0.14, CHCl3)Source of chirality: (R)-1,1′-bi-2-naphthylAbsolute configuration: R
(−)-2,2′,3,3′-Tetraethyl-8,8′-dihydroxy-7,7′-bis(phenanthrene-1,4-dione)C36H30O6Ee >99%[α]D23=-160 (c 0.11, CHCl3)Source of chirality: (R)-1,1′-bi-2-naphthylAbsolute configuration: R
(−)-2,2′,3,3′-Tetraethyl-(8-hydroxy,8′-methoxy)-7,7′-bis(phenanthrene-1,4-dione)C37H32O6Ee >99%[α]D23=-30 (c 0.14, CHCl3)Source of chirality: (R)-1,1′-bi-2-naphthylAbsolute configuration: R
