Application of the Russig-Laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis

Journal of Organic Chemistry

Volumn 65, Issue 3, 2000, Pages 815-822

  Dreher, Spencer D ^a   Katz, Thomas J ^a   Lam, Kin Chung ^b   Rheingold, Arnold L ^b  

^a Columbia University ^*  (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; 1,4 BENZOQUINONE; ALCOHOL; ETHER DERIVATIVE; PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033975070     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991498u     Document Type: Article

References (80)

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45. 2O is added); and (c) irradiating the hydroxyl resonance gave rise to NOEs for the singlet at 7.78 ppm (proton c) and the doublet at 7.57 ppm (proton b), while irradiating the methoxyl's resonance gave an NOE only for proton c.
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52. The double bond between the helicenes is probably trans as in other 2,2′-diphenoquinones, a preference attributed to repulsion of C-O dipoles. Hewgil, F. R.; La Greca, B.; Legge, F.; Roga, P. E. J. Chem. Soc., Perkin Trans. 1 1983, 131.
53. 1H NMR spectra of these compounds are displayed in the Supporting Information.
54. The analysis is related to others (a) in which chiral 1,2-diols were distinguished by menthyldichlorophosphate (Garner, C. M.; McWhorter, C.; Goerke, A. R. Tetrahedron Lett. 1997, 38, 7717), (b) in which the phosphonamide formed from its chlorophosphate and (S)- 1-phenylethylamine was used to determine VAPOLs absolute stereo- chemistry (ref 14c), and (c) [5]HELOLs chlorophosphite was used to distinguish chiral alcohols, amines, and carboxylic acids (Weix, D.; Dreher, S. D.; Katz, T. J. Unpublished results).
55. The analysis is related to others (a) in which chiral 1,2-diols were distinguished by menthyldichlorophosphate (Garner, C. M.; McWhorter, C.; Goerke, A. R. Tetrahedron Lett. 1997, 38, 7717), (b) in which the phosphonamide formed from its chlorophosphate and (S)-1-phenylethylamine was used to determine VAPOLs absolute stereo-chemistry (ref 14c), and (c) [5]HELOLs chlorophosphite was used to distinguish chiral alcohols, amines, and carboxylic acids (Weix, D.; Dreher, S. D.; Katz, T. J. Unpublished results).
56. The analysis is related to others (a) in which chiral 1,2-diols were distinguished by menthyldichlorophosphate (Garner, C. M.; McWhorter, C.; Goerke, A. R. Tetrahedron Lett. 1997, 38, 7717), (b) in which the phosphonamide formed from its chlorophosphate and (S)- 1-phenylethylamine was used to determine VAPOLs absolute stereo- chemistry (ref 14c), and (c) [5]HELOLs chlorophosphite was used to distinguish chiral alcohols, amines, and carboxylic acids (Weix, D.; Dreher, S. D.; Katz, T. J. Unpublished results).
57. 29
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78. 1H NMR spectrum at 4.99 ppm, similar to resonances in the spectra of 1-phenylpropanol (4.52 ppm), 1-(4-chlorophenyl)propanol (4.40 ppm), and 1-(4-methoxyphenyl)propanol (4.47 ppm) was used to analyze for 1-(2-chlorophenyl)propanol.
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