Catalytic asymmetric addition of dialkylzinc to 3,4-dihydroisoquinoline N-oxides utilizing tartaric acid ester as a chiral auxiliary

Bulletin of the Chemical Society of Japan

Volumn 73, Issue 2, 2000, Pages 447-452

  Ukaji, Yutaka ^a   Shimizu, Yuuko ^b   Kenmoku, Yuuichi ^b   Ahmed, Alauddin ^b   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ISOQUINOLINE DERIVATIVE; TARTARIC ACID DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOMER; SYNTHESIS;

EID: 0034048902     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.73.447     Document Type: Article

References (51)

1. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999); R. Bloch, Chem. Rev., 98, 1407 (1998); D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 8, 1895 (1997); S. E. Denmark and O. J.-C. Nicaise, J. Chem. Soc., Chem. Commun., 1996, 999.
2. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999); R. Bloch, Chem. Rev., 98, 1407 (1998); D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 8, 1895 (1997); S. E. Denmark and O. J.-C. Nicaise, J. Chem. Soc., Chem. Commun., 1996, 999.
3. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999); R. Bloch, Chem. Rev., 98, 1407 (1998); D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 8, 1895 (1997); S. E. Denmark and O. J.-C. Nicaise, J. Chem. Soc., Chem. Commun., 1996, 999.
4. S. Kobayashi and H. Ishitani, Chem. Rev., 99, 1069 (1999); R. Bloch, Chem. Rev., 98, 1407 (1998); D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 8, 1895 (1997); S. E. Denmark and O. J.-C. Nicaise, J. Chem. Soc., Chem. Commun., 1996, 999.
5. E. Breuer, "Nitrones, Nitronates and Nitroxides," ed by S. Patai and Z. Rappoport, John Wiley & Sons, Chichester (1989), Chaps. 2 and 3.
6. Recent progresses of enantioselective nucleophilic additions to nitrones: a) S.-I. Murahashi, Y. Imada, K. Harada, Y. Yonemushi, and N. Tomita. "76th National Meeting of the Chemical Society of Japan," Yokohama, March 1999, Abstr., No. 1C130.
7. b) S.-I. Murahashi, S. Watanabe, and T. Shiota, J. Chem. Soc., Chem. Commun., 1994, 725.
8. c) F. L. Merchán, P. Merino, I. Rojo, T. Tejero, and A. Dondoni, Tetrahedron: Asymmetry, 7, 667 (1996).
9. a) Y. Ukaji, Y. Kenmoku, and K. Inomata, Tetrahedron: Asymmetry, 7, 53 (1996).
10. b) Y. Ukaji, T. Hatanaka, A. Ahmed, and K. Inomata, Chem. Lett., 1993, 1313.
11. Enantioselective reactions using tartaric acid esters: Katsuki-Sharpless epoxidation and related epoxidation: a) Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987).
12. b) T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).
13. c) C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald, and P. J. Murray, Angew. Chem., Int. Ed. Engl., 36, 410 (1997).
14. Oxidation of sulfides: d) P. Pitchen, E. Duñach, M. N. Deshmukh, and H. B. Kagan, J. Am. Chem. Soc., 106, 8188 (1984).
15. Allylation and propargylation: e) W. R. Roush, A. E. Walts, and L. K. Hoong, J. Am. Chem. Soc., 107, 8186 (1985).
16. f) N. Ikeda, I. Arai, and H. Yamamoto, J. Am. Chem. Soc., 108, 483 (1986).
17. g) K. Yamada, T. Tozawa, M. Nishida, and T. Mukaiyama, Bull. Chem. Soc. Jpn., 70, 2301 (1997).
18. h) L. C. Zhang, H. Sakurai, and M. Kira, Chem. Lett., 1997, 129.
19. Ring-opening reaction: i) M. Hayashi, K. Ono, H. Hoshimi, and N. Oguni, Tetrahedron, 52, 7817 (1996).
20. Cyanohydrin formation: j) M. Hayashi, T. Matsuda, and N. Oguni, J. Chem. Soc., Perkin Trans. I, 1992, 3135.
21. Diels-Alder reaction: k) A. Ketter, G. Glahsl, and R. Herrmann, J. Chem. Res. (S), 1990, 278.
22. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries: Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023; Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1227; Y. Ukaji, M. Nishimura, and T. Fujisawa, Chem. Lett., 1992, 61.
23. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries: Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023; Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1227; Y. Ukaji, M. Nishimura, and T. Fujisawa, Chem. Lett., 1992, 61.
24. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries: Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023; Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1227; Y. Ukaji, M. Nishimura, and T. Fujisawa, Chem. Lett., 1992, 61.
25. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries: Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023; Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1227; Y. Ukaji, M. Nishimura, and T. Fujisawa, Chem. Lett., 1992, 61.
26. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries: Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023; Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1227; Y. Ukaji, M. Nishimura, and T. Fujisawa, Chem. Lett., 1992, 61.
27. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries: Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023; Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1227; Y. Ukaji, M. Nishimura, and T. Fujisawa, Chem. Lett., 1992, 61.
28. Preliminary work of the enantioselective addition of dialkylzinc to nitrones utilizing tartaric acid ester as a chiral auxiliary has been briefly reported as a communication: Y. Ukaji, Y. Shimizu, Y. Kenmoku, A. Ahmed, and K. Inomata, Chem. Lett., 1997, 59.
29. When 2.0 molar amounts of diethylzinc were reacted with nitrone 1a in the presence of 0.1 molar amount of 2a and 0.1 molar amount of 2b, enantioselectivity of the product 3a was 19% ee. From this result, possibility of disproportionation of 2c to 2a and 2b can be excluded.
30. In these reactions, the corresponding methylated hydroxylamine 3b was scarcely obtained.
31. 7 were incorrect. They should be corrected as described in Table 2 in this manuscript.
32. The stereochemical course of dialkylzinc in the asymmetric addition to aldehyde was discussed: a) R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991).
33. b) K. Soai and S. Niwa, Chem. Rev., 92, 833 (1992).
34. c) H. Kitajima, K. Ito, Y. Aoki, and T. Katsuki, Bull. Chem. Soc. Jpn., 70, 207 (1997).
35. The possibility of the alkyl group bridging between metals in organozincs was noted: J. Boersma, "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, Pergamon Press, Oxford (1982), Vol. 2, p. 827.
36. M. E. Bembenek, C. W. Abell, L. A. Chrisey, M. D. Rozwadowska, W. Gessner, and A. Brossi, J. Med. Chem., 33, 147 (1990).
37. A. R. Battersby and T. P. Edwards, J. Chem. Soc., 1960, 1214.
38. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
39. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
40. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
41. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
42. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
43. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
44. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
45. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
46. Recent reports on the asymmetric synthesis of salsolidine: N. Yamazaki, H. Suzuki, S. Aoyagi, and C. Kibayashi, Tetrahedron Lett., 37, 6161 (1996); V. L. Ponzo and T. S. Kaufman, Tetrahedron Lett., 36, 9105 (1995); T. Morimoto, N. Nakajima, and K. Achiwa, Synlett, 1995, 748; C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994); M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); R. P. Polniaszek and C. R. Kaufman, J. Am. Chem. Soc., 111, 4859 (1989); A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); R. Noyori, M. Ohta, Y. Hisao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986), and Ref. 3b.
47. 4b
48. "Isoquinolines," ed by G. Grethe, John Wiley & Sons, Inc., New York (1981).
49. S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 55, 1736 (1990).
50. S. Ruchirawat, M. Chaisupakitsin, N. Patranuwatana, J. L. Cashaw, and V. E. Davis, Synth. Commun., 14, 1221 (1984).
51. G. Uray and W. Lindner, Tetrahedron, 44, 4357 (1988).