A novel aryl migration from silicon to carbon: An efficient approach to asymmetric synthesis of α-aryl β-hydroxy cyclic amines and silanols

Journal of the American Chemical Society

Volumn 122, Issue 2, 2000, Pages 408-409

  Tomooka, Katsuhiko ^a   Nakazaki, Atsuo ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; SILICON;

ARTICLE; CHIRALITY; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; SIALYLATION; STEREOCHEMISTRY;

EID: 0033966964     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993295t     Document Type: Article

References (31)

1. The Alkaloids, Chemistry and Biology; Cordell, G. A., Ed.; Academic: San Diego, 1998; Vol. 50.
2. For a recent example, see: Batey, R. A.; MacKay, D. B.; Santhakumar, V. J. Am. Chem. Soc. 1999, 121, 5075-5076 and references therein.
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8. Tomooka, K.; Yamamoto, H.; Nakai, T. J. Am. Chem. Soc. 1996, 118, 3317-3318.
9. 4/MeOH. (S)-3-Hydroxypyrrolidin-2-one was prepared according to the literature procedure: Sarairi, D.; Maurey, G. Bull. Soc. Chim. Fr. 1987, 297-301. The details are described in the Supporting Information.
10. (a) Trost, B. M.; Edstrom, E. D. Angew. Chem., Int. Ed. Engl. 1990, 29, 520-522.
11. (b) Tomooka, K.; Nakamura, Y.; Nakai, T. Synlett 1995, 321-322.
12. 1H NMR analysis.
13. The structure of 3a was determined by X-ray crystallography, see the Supporting Information.
14. The product ratio depended upon the reaction time: aminal 2a (26% for 1 h. and 13% for 12 h) and α-phenylpyrrolidine 3a (36% for 1 h and 46% for 12 h). Obviously, aminal 2a initially formed is gradually converted to 3a under the reaction conditions.
15. The absolute configuration of (S)-4a was assigned from the stereochemistry of 3a, based on the reasonable postulate that the β-elimination proceeds without loss of the configurational integrity at the silicon. The enantiomeric excess of 4a and 4b was determined by HPLC analysis using a Daicel CHIRACEL OD column with hexane/2-propanol as a solvent.
16. 2/Pd-C) to 8e (eq 5, R = H).
17. (a) Harrison, T.; Williams, B. J.; Swain, C. J.; Ball, R. G. Bioorg. Med. Chem. Lett. 1994, 4, 2545-2550.
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19. This compound was prepared from (S)-hydroxypyrrolidin-2-one in a manner similar to 1. The corresponding silyl ether was derived from tertbutylbis(4-methylphenyl)silanol and (S)-hydroxypyrrolidin-2-one in the presence of oxalyl chloride according to the literature procedure: Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206-4207. Lennon, P. J., Mack, D. P.; Thompson, Q. E. Organometallics 1989, 8, 1121-1122.
20. This compound was prepared from (S)-hydroxypyrrolidin-2-one in a manner similar to 1. The corresponding silyl ether was derived from tertbutylbis(4-methylphenyl)silanol and (S)-hydroxypyrrolidin-2-one in the presence of oxalyl chloride according to the literature procedure: Tanino, K.; Yoshitani, N.; Moriyama, F.; Kuwajima, I. J. Org. Chem. 1997, 62, 4206- 4207. Lennon, P. J., Mack, D. P.; Thompson, Q. E. Organometallics 1989, 8, 1121-1122.
21. Related example of intramoleculer Friedel-Crafts reaction, see: Martin, O. R.; Rao, S. P.; Kurz, K. G.; El-Shenawy, H. A. J. Am. Chem. Soc. 1988, 110, 8698-8700.
22. Related examples of phenyl migration reaction from silicon to carbon have been reported. For 1,4- or 1,5-phenyl or vinyl migration promoted by Lewis acids, see: (a) Archibald, S. C.; Fleming, I. Tetrahedron Lett. 1993, 34, 2387-2390. (b) Hioki, H.; Izawa, T.; Yoshizuka, M.; Kunitake, R.; Ito, S. Tetrahedron Lett. 1995, 36, 2289-2992. For 1,2-phenyl migration promoted by fluoride ion, see: (c) Morihata, K.; Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5555-5558.
23. Related examples of phenyl migration reaction from silicon to carbon have been reported. For 1,4- or 1,5-phenyl or vinyl migration promoted by Lewis acids, see: (a) Archibald, S. C.; Fleming, I. Tetrahedron Lett. 1993, 34, 2387-2390. (b) Hioki, H.; Izawa, T.; Yoshizuka, M.; Kunitake, R.; Ito, S. Tetrahedron Lett. 1995, 36, 2289-2992. For 1,2-phenyl migration promoted by fluoride ion, see: (c) Morihata, K.; Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5555-5558.
24. Related examples of phenyl migration reaction from silicon to carbon have been reported. For 1,4- or 1,5-phenyl or vinyl migration promoted by Lewis acids, see: (a) Archibald, S. C.; Fleming, I. Tetrahedron Lett. 1993, 34, 2387-2390. (b) Hioki, H.; Izawa, T.; Yoshizuka, M.; Kunitake, R.; Ito, S. Tetrahedron Lett. 1995, 36, 2289-2992. For 1,2-phenyl migration promoted by fluoride ion, see: (c) Morihata, K.; Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5555-5558.
25. Obviously, more detailed studies are needed to elucidate the exact mechanism, particularly concerning the specific role of K10 and the steric course of the substitution on the silicon. Semiempirical calculations on the transition states are underway.
26. A few synthetic methods for enantio-enriched silanol have been reported. For resolution or separation of racemic or diastereomeric silanols, see: (a) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237. (b) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437. (c) Feibush, B.; Woolley, C. L.; Mani, V. Anal. Chem. 1993, 65, 1130-1133. (d) Mori, A.; Toriyama, F.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550. For stereospecific oxidation of enantio-enriched silanes or halosilanes, see: (e) Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097-2103 and references therein.
27. A few synthetic methods for enantio-enriched silanol have been reported. For resolution or separation of racemic or diastereomeric silanols, see: (a) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237. (b) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437. (c) Feibush, B.; Woolley, C. L.; Mani, V. Anal. Chem. 1993, 65, 1130-1133. (d) Mori, A.; Toriyama, F.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550. For stereospecific oxidation of enantio-enriched silanes or halosilanes, see: (e) Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097-2103 and references therein.
28. A few synthetic methods for enantio-enriched silanol have been reported. For resolution or separation of racemic or diastereomeric silanols, see: (a) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237. (b) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437. (c) Feibush, B.; Woolley, C. L.; Mani, V. Anal. Chem. 1993, 65, 1130-1133. (d) Mori, A.; Toriyama, F.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550. For stereospecific oxidation of enantio-enriched silanes or halosilanes, see: (e) Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097-2103 and references therein.
29. A few synthetic methods for enantio-enriched silanol have been reported. For resolution or separation of racemic or diastereomeric silanols, see: (a) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237. (b) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437. (c) Feibush, B.; Woolley, C. L.; Mani, V. Anal. Chem. 1993, 65, 1130-1133. (d) Mori, A.; Toriyama, F.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550. For stereospecific oxidation of enantio-enriched silanes or halosilanes, see: (e) Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097-2103 and references therein.
30. A few synthetic methods for enantio-enriched silanol have been reported. For resolution or separation of racemic or diastereomeric silanols, see: (a) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237. (b) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437. (c) Feibush, B.; Woolley, C. L.; Mani, V. Anal. Chem. 1993, 65, 1130-1133. (d) Mori, A.; Toriyama, F.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550. For stereospecific oxidation of enantio-enriched silanes or halosilanes, see: (e) Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097-2103 and references therein.
31. A few synthetic methods for enantio-enriched silanol have been reported. For resolution or separation of racemic or diastereomeric silanols, see: (a) Tacke, R.; Linoh, H.; Ernst, L.; Moser, U.; Mutschler, E.; Sarge, S.; Cammenga, H. K.; Lambrecht, G. Chem. Ber. 1987, 120, 1229-1237. (b) Yamamoto, K.; Kawanami, Y.; Miyazawa, M. J. Chem. Soc., Chem. Commun. 1993, 436-437. (c) Feibush, B.; Woolley, C. L.; Mani, V. Anal. Chem. 1993, 65, 1130-1133. (d) Mori, A.; Toriyama, F.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1999, 549-550. For stereospecific oxidation of enantio-enriched silanes or halosilanes, see: (e) Cavicchioli, M.; Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 6329-6330. (f) Adam, W.; Mitchell, C. M.; Saha-Möller, C. R.; Weichold, O. J. Am. Chem. Soc. 1999, 121, 2097-2103 and references therein.