Asymmetric addition reaction of organozinc reagents to nitrones using a catalytic amount of external chiral auxiliary

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 53-56

  Ukaji, Yutaka ^a   Kenmoku, Yuuichi ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLAMINE; ISOQUINOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030069086     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00419-X     Document Type: Article

References (21)

1. Y. Ukaji, T. Hatanaka, A. Ahmed, and K. Inomata, Chem. Lett., 1993, 1313.
2. K. Tomioka, Synthesis, 1990, 541; R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); K. Soai and S. Niwa, Chem, Rev., 92, 833 (1992) and references cited therein.
3. K. Tomioka, Synthesis, 1990, 541; R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); K. Soai and S. Niwa, Chem, Rev., 92, 833 (1992) and references cited therein.
4. K. Tomioka, Synthesis, 1990, 541; R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991); K. Soai and S. Niwa, Chem, Rev., 92, 833 (1992) and references cited therein.
5. I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429 (1994); K. Soai, T. Suzuki, and T. Shono, J. Chem. Soc., Chem. Commun., 1994, 317; S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797 (1994) and references cited therein.
6. I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429 (1994); K. Soai, T. Suzuki, and T. Shono, J. Chem. Soc., Chem. Commun., 1994, 317; S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797 (1994) and references cited therein.
7. I. Inoue, M. Shindo, K. Koga, and K. Tomioka, Tetrahedron, 50, 4429 (1994); K. Soai, T. Suzuki, and T. Shono, J. Chem. Soc., Chem. Commun., 1994, 317; S. E. Denmark, N. Nakajima, and O. J.-C. Nicaise, J. Am. Chem. Soc., 116, 8797 (1994) and references cited therein.
8. Recent reports on asymmetric synthesis using nitrones: a) S.-I. Murahashi, Y. Imada, M. Kohno, and T, Kawanami, Synlett, 1993, 395; b) S.-I. Murahashi, J. Sun, and T. Tsuda, Tetrahedron Lett., 34, 2645 (1993); c) S.-I. Murahashi, S. Watanabe, and T. Shiota, J. Chem. Soc., Chem. Commun., 1994, 725.
9. Recent reports on asymmetric synthesis using nitrones: a) S.-I. Murahashi, Y. Imada, M. Kohno, and T, Kawanami, Synlett, 1993, 395; b) S.-I. Murahashi, J. Sun, and T. Tsuda, Tetrahedron Lett., 34, 2645 (1993); c) S.-I. Murahashi, S. Watanabe, and T. Shiota, J. Chem. Soc., Chem. Commun., 1994, 725.
10. Recent reports on asymmetric synthesis using nitrones: a) S.-I. Murahashi, Y. Imada, M. Kohno, and T, Kawanami, Synlett, 1993, 395; b) S.-I. Murahashi, J. Sun, and T. Tsuda, Tetrahedron Lett., 34, 2645 (1993); c) S.-I. Murahashi, S. Watanabe, and T. Shiota, J. Chem. Soc., Chem. Commun., 1994, 725.
11. Nitrones 1 were prepared from the corresponding tetrahydroisoquinolines: S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 55, 1736 (1990).
12. Catalytic asymmetric addition reaction of organozinc reagents to aldehydes using Chirald® was reported: G. Muchow, Y. Vannoorenberghe, and G. Buono, Tetrahedron Lett., 28, 6163 (1987); E. Laloë and M. Srebnik, ibid., 35, 5587 (1994).
13. Catalytic asymmetric addition reaction of organozinc reagents to aldehydes using Chirald® was reported: G. Muchow, Y. Vannoorenberghe, and G. Buono, Tetrahedron Lett., 28, 6163 (1987); E. Laloë and M. Srebnik, ibid., 35, 5587 (1994).
14. Butylmagnesium bromide or phenylmagnesium bromide was used.
15. Previously we reported that the reaction of diethylzinc with 1A in the presence of 2 gave 3a in 57% ee.1) After further experiments, the use of fairly purified crystalline 1A was found to realize higher selection.
16. Recent reports on the asymmetric synthesis of salsolidine: a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986); b) R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); c) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); d) R. P. Polniaszck and C. R. Kaufman, J. Am. Chem. Soc, 111, 4859 (1989); e) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); f) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994).
17. Recent reports on the asymmetric synthesis of salsolidine: a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986); b) R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); c) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); d) R. P. Polniaszck and C. R. Kaufman, J. Am. Chem. Soc, 111, 4859 (1989); e) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); f) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994).
18. Recent reports on the asymmetric synthesis of salsolidine: a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986); b) R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); c) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); d) R. P. Polniaszck and C. R. Kaufman, J. Am. Chem. Soc, 111, 4859 (1989); e) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); f) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994).
19. Recent reports on the asymmetric synthesis of salsolidine: a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986); b) R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); c) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); d) R. P. Polniaszck and C. R. Kaufman, J. Am. Chem. Soc, 111, 4859 (1989); e) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); f) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994).
20. Recent reports on the asymmetric synthesis of salsolidine: a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986); b) R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); c) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); d) R. P. Polniaszck and C. R. Kaufman, J. Am. Chem. Soc, 111, 4859 (1989); e) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); f) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994).
21. Recent reports on the asymmetric synthesis of salsolidine: a) R. Noyori, M. Ohta, Y. Hsiao, M. Kitamura, T. Ohta, and H. Takaya, J. Am. Chem. Soc., 108, 7117 (1986); b) R. E. Gawley, G. Hart, M. Goicoechea-Pappas, and A. L. Smith, J. Org. Chem., 51, 3076 (1986); c) A. I. Meyers, D. A. Dickman, and M. Boes, Tetrahedron, 43, 5095 (1987); d) R. P. Polniaszck and C. R. Kaufman, J. Am. Chem. Soc, 111, 4859 (1989); e) M. Yamato, K. Hashigaki, N. Qais, and S. Ishikawa, Tetrahedron, 46, 5909 (1990); f) C. A. Willoughby and S. L. Buchwald, J. Am. Chem. Soc., 116, 11703 (1994).