The synthesis of enantiomerically pure 4-substituted [2.2]paracyclophane derivatives by sulfoxide–metal exchange

Hitchcock, Peter B.; Rowlands, Gareth J.; Parmar, Rakesh

doi:10.1039/b507394d

Cited by 58 publications

(41 citation statements)

References 23 publications

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“…[(tht)AuCl] [38] (tht = tetrahydrothiophene) and Ph 2 -GemPhos [11] were prepared according to modified standard procedures. THF was distilled under nitrogen from potassium benzophenone ketyl prior to use.…”

Section: Methodsmentioning

confidence: 99%

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[2.2]Paracyclophanediyldiphosphane Complexes of Gold

et al. 2012

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We have prepared digold(I) complexes with the rigid-backbone diphosphane ligands PhanePhos, xyl-PhanePhos, and Ph 2 -GemPhos. All complexes were characterized by singlecrystal X-ray diffraction, NMR, IR, Raman, and photoluminescence (PL) spectroscopy. [PhanePhos(AuCl) 2 ] and [Gem-Phos(AuCl) 2 ] show a very similar ligand scaffold, but different (aurophilic vs. nonaurophilic) intramolecular Au-Au distances. Absorption and PL spectra of both compounds are quite similar. Theoretical investigations reveal that the excited states are of different character (i.e., influenced by the Au-Au contacts). The respective transition energies, however, lie close to each other, thus resulting in similar experi-

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Section: Methodsmentioning

confidence: 99%

“…Thus, the signal of the ligand [δ( 31 P) = -0.53 (PhanePhos), [6a] -2.0 (xyl-PhanePhos), [6b] and -7.78 ppm (GemPhos) [11] ] is shifted to δ( 31 P) = 30.7 (1), 31.5 (2), and 29.7 ppm (3), respectively. The 1 H and 13 C{ 1 H} NMR spectra show the expected set of signals.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

[2.2]Paracyclophanediyldiphosphane Complexes of Gold

et al. 2012

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“…New routes to planar chiral molecules can only increase the utility of these compounds. [3][4][5] [2.2]Paracyclophane provides a versatile platform for the synthesis of planar chiral molecules and such compounds have found use in asymmetric synthesis [6][7][8] and the development of new materials and polymers. [2,[9][10][11][12] Many racemic heterocyclic [2.2] paracyclophane derivatives have been reported but few have been resolved and as a result their full potential has not been realised.…”

Section: Introductionmentioning

confidence: 99%

An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis

Thennakoon¹,

Kaur²,

Wang³

et al. 2015

Aust. J. Chem.

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Enantiomerically enriched planar chiral indoles were prepared by an asymmetric variant of the Bischler-Möhlau synthesis. Cinchonine was used as a 'traceless' resolving reagent, allowing the formation of readily separable quaternary ammonium salts that were the key intermediates in the indole synthesis. The condensation of the ammonium salt and various substituted anilines was achieved under microwave irradiation; this reduced reaction times and minimised racemisation. The utility of the indoles was demonstrated by their transformation into monophosphane ligands that were capable of coupling challenging substrates in the Suzuki-Miyaura reaction.

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“…Our main interest in the chemistry of [2.2]paracyclophane has been the development of new methodology for the synthesis of enantiopure derivatives 7–9. This has led us to investigate their application in catalysis, and we have gained an interest in the synthesis and activity of planar chiral phosphines 10–16.…”

Section: Introductionmentioning

confidence: 99%

Planar Chiral Phosphines Derived from [2.2]Paracyclophane

Rowlands

2012

Israel Journal of Chemistry

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radicals and, of course, the chemistry of [2.2]paracyclophane. He lives with his partner, Kate, two insane cats and an ever growing pile of cds and books that he has no hope of ever finishing. Scheme 2. Reduction of a tetrahydropyrazine. Reaction conditions: (a) 12 a (2 mol %), H 2 (1.5 atm), À40 8C, 6 h, > 99 %, 86 % ee. The absolute stereochemistry of 14 is not given in ref. [6]. Scheme 3. Synthesis of diaryl amino acid. Reaction conditions: (a) [(R)-12 a-Rh(cod)]BF 4 (0.4 mol %), H 2 (10 atm), rt, > 99 %, 89 % ee.

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The synthesis of enantiomerically pure 4-substituted [2.2]paracyclophane derivatives by sulfoxide–metal exchange

Abstract: A general strategy for the synthesis of enantiomerically pure 4-substituted [2.2]paracyclophanes from a common sulfoxide precursor is described.

Cited by 58 publications

References 23 publications

[2.2]Paracyclophanediyldiphosphane Complexes of Gold

[2.2]Paracyclophanediyldiphosphane Complexes of Gold

An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis

Planar Chiral Phosphines Derived from [2.2]Paracyclophane

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