Asymmetric addition of a Reformatsky-type reagent to 3,4-dihydroisoquinoline N-oxides

Tetrahedron Asymmetry

Volumn 11, Issue 3, 2000, Pages 733-736

  Ukaji, Yutaka ^a,b   Yoshida, Yayoi ^a   Inomata, Katsuhiko ^a,b  

^a KANAZAWA UNIVERSITY   (Japan)

^b Kanazawa University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; REAGENT;

ARTICLE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0034712184     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00003-3     Document Type: Article

References (32)

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4. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183; Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952; Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725; Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117; Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265.
5. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183; Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952; Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725; Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117; Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265.
6. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183; Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952; Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725; Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117; Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265.
7. Morimoto, T.; Suzuki, N.; Achiwa, K. Tetrahedron: Asymmetry 1998, 9, 183; Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952; Murahashi, S.-I.; Watanabe, S.; Shiota, T. J. Chem. Soc., Chem. Commun. 1994, 725; Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117; Yamada, K.; Takeda, M.; Iwakuma, T. J. Chem. Soc., Perkin Trans. 1 1983, 265.
8. (a) Nakamura, M.; Hirai, A.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 8489.
9. (b) Murahashi, S.-I.; Imada, Y.; Harada, K.; Yonemushi, Y.; Tomita, N. 76th National Meeting of the Chemical Society of Japan, Yokohama, March 1999, Abstract, 1C130.
10. Asymmetric synthesis of chiral α-substituted benzylamines followed by the cyclization was also reported: Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron: Asymmetry 1999, 10, 221; Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105.
11. Asymmetric synthesis of chiral α-substituted benzylamines followed by the cyclization was also reported: Taniyama, D.; Hasegawa, M.; Tomioka, K. Tetrahedron: Asymmetry 1999, 10, 221; Ponzo, V. L.; Kaufman, T. S. Tetrahedron Lett. 1995, 36, 9105.
12. Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, A.; Inomata, K. Chem. Lett. 1997, 59; Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, A.; Inomata, K. Bull. Chem. Soc. Jpn., in press.
13. Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, A.; Inomata, K. Chem. Lett. 1997, 59; Ukaji, Y.; Shimizu, Y.; Kenmoku, Y.; Ahmed, A.; Inomata, K. Bull. Chem. Soc. Jpn., in press.
14. Rathke, M. W. Org. React. 1975, 22, 423: see also Ref. 12.
15. Reaction of dialkylzinc with α-halo carbonyl compounds was reported to generate zinc enolate equivalents: Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1962, 1762; Hansen, M. M.; Bartlett, P. A.; Heathcock, C. H. Organometallics 1987, 6, 2069; Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463.
16. Reaction of dialkylzinc with α-halo carbonyl compounds was reported to generate zinc enolate equivalents: Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1962, 1762; Hansen, M. M.; Bartlett, P. A.; Heathcock, C. H. Organometallics 1987, 6, 2069; Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463.
17. Reaction of dialkylzinc with α-halo carbonyl compounds was reported to generate zinc enolate equivalents: Palmer, M. H.; Reid, J. A. J. Chem. Soc. 1962, 1762; Hansen, M. M.; Bartlett, P. A.; Heathcock, C. H. Organometallics 1987, 6, 2069; Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463.
18. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
19. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
20. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
21. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
22. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
23. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
24. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
25. Asymmetric additions of enolate or its equivalent to a carbon-nitrogen double bond in the presence of external chiral auxiliary were reported: Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450; Tomioka, K.; Fujieda, H.; Hayashi, S.; Hussein, M. A.; Kambara, T.; Nomura, Y.; Kanai, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1999, 715; Ferraris, D.; Young, B.; Cox, C.; Drury III, W. J.; Dudding, T.; Lectka, T. J. Org. Chem. 1998, 63, 6090; Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131; Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153; Fujieda, H.; Kanai, M.; Kambara, T.; Iida, A.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 2060; Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10 520; Corey, E. J.; Decicco, C. P.; Newbold, R. C. Tetrahedron Lett. 1991, 32, 5287, and Ref. 4b.
26. 1H NMR spectra, IR spectra, and elemental analyses or MS spectra.
27. 25 +33 (c 1.00, MeOH).
28. It was reported that the Reformatsky reagent possesses a C-Zn character and/or O-Zn character: Vaughan, W. R.; Bernstein, S. C.; Lorber, M. E. J. Org. Chem. 1965, 30, 1790; Dekker, J.; Boersma, J.; van der Kerk, G. J. M. J. Chem. Soc., Chem. Commun. 1983, 553; Dekker, J.; Budzelaar, P. H. M.; Boersma, J.; van der Kerk, G. J. M.; Spek, A. L. Organometallics 1984, 3, 1403, and references cited therein.
29. It was reported that the Reformatsky reagent possesses a C-Zn character and/or O-Zn character: Vaughan, W. R.; Bernstein, S. C.; Lorber, M. E. J. Org. Chem. 1965, 30, 1790; Dekker, J.; Boersma, J.; van der Kerk, G. J. M. J. Chem. Soc., Chem. Commun. 1983, 553; Dekker, J.; Budzelaar, P. H. M.; Boersma, J.; van der Kerk, G. J. M.; Spek, A. L. Organometallics 1984, 3, 1403, and references cited therein.
30. It was reported that the Reformatsky reagent possesses a C-Zn character and/or O-Zn character: Vaughan, W. R.; Bernstein, S. C.; Lorber, M. E. J. Org. Chem. 1965, 30, 1790; Dekker, J.; Boersma, J.; van der Kerk, G. J. M. J. Chem. Soc., Chem. Commun. 1983, 553; Dekker, J.; Budzelaar, P. H. M.; Boersma, J.; van der Kerk, G. J. M.; Spek, A. L. Organometallics 1984, 3, 1403, and references cited therein.
31. Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53; Stereochemistry Abstracts A18.
32. Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1996, 7, 53; Stereochemistry Abstracts A18.