Asymmetric O- and C-alkylation of phenols

Journal of the American Chemical Society

Volumn 120, Issue 4, 1998, Pages 815-816

  Trost, Barry M ^a   Toste, F Dean ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY; STEREOSPECIFICITY; TEMPERATURE;

EID: 0032481394     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972453i     Document Type: Article

References (43)

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2. For reviews, see: (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 827-874. (b) Moody, C. J. Adv. Heterocycl. Chem. 1987, 42, 203. (c) Lutz, R. P. Chem. Rev. 1984, 84, 205. (d) Bennett, G. B. Synthesis 1977, 589. (e) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 22, 1.
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22. All new compounds have been satisfactorily characterized spectroscopically.
23. 3 (8 mg, 0.008 mmol) in minimal dry chloroform (0.1 mL), under nitrogen, was placed into a preheated 50°C oil bath for 8 h. After cooling, direct flash chromatography, eluting with 5:1 petroleum ether:ether, afforded 13c (160 mg, 91% yield) as a colorless liquid. For larger scale reactions, better results were obtained by diluting the reaction mixture with ether and washing with water to remove the europium catalyst prior to chromatography.
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27. 3 in hetero-Diels-Alder cycloadditions, see: Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. And in epoxide rearrangements, see: Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 5321.
28. 3 in hetero-Diels-Alder cycloadditions, see: Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716. And in epoxide rearrangements, see: Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 5321.
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33. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. M.; Balkovec, J. M.; Baldwin, J. J.; Christry, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370. Latypou, S. K. Seco, J. M.; Quinoa, E.; Riguera, R. J. Org. Chem. 1996, 61, 8569.
34. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. M.; Balkovec, J. M.; Baldwin, J. J.; Christry, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370. Latypou, S. K. Seco, J. M.; Quinoa, E.; Riguera, R. J. Org. Chem. 1996, 61, 8569.
35. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
36. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
37. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
38. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
39. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
40. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
41. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
42. For a few illustrations, see: ref 8. Hosokawa, T.; Murahashi, S. I. J. Synth. Org. Chem. Jpn. 1995, 53, 1009; Heterocycles 1992, 33, 1079; Acc. Chem. Res. 1990, 23, 49. Youssefyeh, R. D.; Campbell, H. F.; Airey, J. E.; Klein, S.; Schnapper, M.; Powers, M.; Woodward, R.; Rodriguez, W.; Golec, B.; Studt, W.; Dodson, S. A.; Fitzpatrick, L. R.; Pendley, C. E.; Martin, G. E. J. Med. Chem. 1992, 35, 903. Bernard, A. M.; Cocco, M. T.; Onnis, V.; Piras, P. P. Synthesis 1997, 41. Also, see: Parker, K. A.; Fokas, D. J. Org. Chem. 1994, 59, 3927. Larock, R. C.; Lee, N. H. J. Org. Chem. 1991, 56, 6253. Nagase, H.; Matsumoto; Yoshiwara, H.; Tajima, A.; Ohno, K. Tetrahedron Lett. 1990, 31, 4493.
43. During the preparation of this manuscript, use of a stoichiometric chiral Lewis acid to mediate rearrangement of achiral substrates derived from catechol was reported, see: Ito, H.; Sato, A.; Taguchi, T. Tetrahedron Lett. 1997, 38, 14815.