Highly selective oxidative cross-coupling of substituted 2-naphthols: A convenient approach to unsymmetrical 1,1′-binaphthalene-2,2′-diols

Hovorka, Martin; Günterová, Jana; Závada, Jiřı́

doi:10.1016/s0040-4039(00)94569-6

Cited by 105 publications

(45 citation statements)

References 17 publications

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“…These crosscoupling selectivities are consistent with those observed for the polymerization, and the stereostructure of the cross coupling compound, 9, obtained with (S)Phbox is identical with that preferentially constructed during the polymerization. Therefore, the polymerization with the CuCl-(S)Phbox catalyst in the presence of Yb(OTf) 3 should proceed with about the observed selectivity for this model reaction. The CD spectrum of the obtained 9 is shown in Figure 3.…”

Section: Resultsmentioning

confidence: 97%

“…The results are summarized in Table III (Scheme 6). When Yb(OTf) 3 was used for the polymerization, a much longer reaction time was needed to attain a good polymer yield, and the M n value was also reduced, in comparison with that of the polymers obtained without Yb(OTf) 3 . Those results are different from those for the polymerization of 2.…”

Section: Resultsmentioning

confidence: 97%

“…Therefore, Figure 3. CD spectra of the cross-coupling compounds 9 obtained with CuCl-(S )Phbox in the presence of Yb(OTf) 3 (Table II, entry 2) (binaphthalene unit, in THF). both catalysts cooperate in the cross-coupling intermediate.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6] Recently, we found that a catalytic asymmetric oxidative coupling between 2-naphthol and 3-hydroxy-2-naphthoate derivatives using CuCl-(S)-2,2 0 -isopropylidenebis-(4-phenyl-2-oxazoline) [CuCl-(S)Phbox] (Scheme 1) proceeds in a highly cross-coupling selective manner. [7][8][9][10] This was further used for the polymerization of the unsymmetric 6,6 0 -bi-2-naphthol derivatives, such as 1 (Scheme 2), to give poly(BINOL), [11][12][13][14] which is interesting as an optically active and electroluminescent material, etc.…”

mentioning

confidence: 99%

“…On the other hand, a Lewis acid catalyst, such as the trifluoromethanesulfonate salts of ytterbium and scandium [Yb(OTf) 3 and Sc(OTf) 3 ], is often used as an effective tool for selectivity control during the radical reaction, especially, the radical addition process. [21][22][23][24][25][26][27] Therefore, in our initial study, the oxidative coupling reaction of the 2-naphthol and 3-hydroxy-2-naphthoate derivatives with a copper catalyst in the presence of Yb(OTf) 3 was examined, and a significant effect on controlling both the cross-coupling and stereoselectivity was observed.…”

mentioning

confidence: 99%

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Lewis-Acid-Assisted Highly Selective Oxidative Cross-Coupling Polymerization with Copper Catalysts

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Lewis-Acid-Assisted Highly Selective Oxidative Cross-Coupling Polymerization with Copper Catalysts

Pei

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Molecular Recognition of Pyranosides by a Family of Trimeric, 1,1′-Binaphthalene-Derived Cyclophane Receptors

Bähr¹,

Droz²,

Püntener³

et al. 1998

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Asymmetric Phase-Transfer Catalysis by Quaternary Ammonium Ions Derived fromCinchona-Alkaloid Analogs Containing 1,1′-Binaphthalene Moieties

Ducry¹,

Diederich²

1999

HCA

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The synthesis and catalytic properties of a new type of enantioselective phase‐transfer catalysts, incorporating both the quinuclidinemethanol fragment of Cinchona alkaloids and a 1,1′‐binaphthalene moiety, are described. Catalyst (+)‐(aS,3R,4S,8R,9S)‐4 with the quinuclidine fragment attached to C(7′) in the major groove of the 1,1′‐binaphthalene residue was predicted by computer modeling to be an efficient enantioselective catalyst for the unsymmetric alkylation of 6,7‐dichloro‐5‐methoxy‐2‐phenylindanone (1; Scheme 1, Fig. 1). Its synthesis involved the selective oxidative cross‐coupling of two differently substituted naphthalen‐2‐ols to afford the asymmetrically substituted 1,1′‐binaphthalene derivative (±)‐17 in high yield (Scheme 3). Chromatographic optical resolution via formation of diastereoisomeric camphorsulfonyl esters and functional‐group manipulation gave access to the 7‐bromo‐1,1′‐binaphthalene derivative (−)‐(aS)‐11 (Scheme 4). Nucleophilic addition of lithiated (−)‐(aS)‐11 to the quinuclidine Weinreb amide (+)‐(3R,4S,8R)‐8 afforded the two ketones (aS,3R,4S,8R)‐27 and (aS,3R,4S,8S)‐28 as an inseparable mixture of diastereoisomers (Scheme 6). Stereoselective reduction of this mixture with DIBAL‐H (diisobutylaluminum hydride; preferred formation of the C(8)−C(9) erythro‐pair of diastereoisomers with 18% de) or with NaBH4 (preferred formation of the threo‐pair of diastereoisomers with 50% de) afforded the four separable diastereoisomers (+)‐(aS,3R,4S,8S,9S)‐29, (+)‐(aS,3R,4S,8R,9R)‐30, (−)‐(aS,3R,4S,8S,9R)‐31, and (+)‐(aS,3R,4S,8R,9S)‐32 (Scheme 6). A detailed conformational analysis, combining 1H‐NMR spectroscopy and molecular‐mechanics computations, revealed that the four diastereoisomers displayed distinctly different conformational preferences (Figs. 2 and 3). These novel Cinchona‐alkaloid analogs were quaternized to give (+)‐(aS,3R,4S,8R,9S)‐4, (+)‐(aS,3R,4S,8S,9S)‐5, (+)‐(aS,3R,4S,8R,9R)‐6, and (−)‐(aS,3R,4S,8S,9R)‐7 (Scheme 7) which were tested as phase‐transfer agents in the asymmetric allylation of phenylindanone 1. Without any optimization work, (+)‐(aS,3R,4S,8R,9S)‐4 was found to catalyze the allylation of 1 yielding the predicted enantiomer (+)‐(S)‐3b in 32% ee. The three diastereoisomeric catalysts (+)‐5, (+)‐6, and (−)‐7 gave access to lower enantioselectivities (6 to 22% ee's), which could be rationalized by computer modeling (Fig. 4).

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Highly selective oxidative cross-coupling of substituted 2-naphthols: A convenient approach to unsymmetrical 1,1′-binaphthalene-2,2′-diols

Cited by 105 publications

References 17 publications

Lewis-Acid-Assisted Highly Selective Oxidative Cross-Coupling Polymerization with Copper Catalysts

Lewis-Acid-Assisted Highly Selective Oxidative Cross-Coupling Polymerization with Copper Catalysts

Molecular Recognition of Pyranosides by a Family of Trimeric, 1,1′-Binaphthalene-Derived Cyclophane Receptors

Asymmetric Phase-Transfer Catalysis by Quaternary Ammonium Ions Derived fromCinchona-Alkaloid Analogs Containing 1,1′-Binaphthalene Moieties

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