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Volumn 64, Issue 13, 1999, Pages 4610-4616

A new general method for the asymmetric synthesis of 4-alkyl-3-aryl- 1,2,3,4-tetrahydroisoquinolines

Author keywords

[No Author keywords available]

Indexed keywords

4 ALKYL 3 ARYL 1,2,3,4 TETRAHYDROISOQUINOLINE; ALPHA ALKYLARYLACETIC ACID DERIVATIVE; ARYLACETIC ACID DERIVATIVE; PSEUDOEPHEDRINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033603369     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982008l     Document Type: Article
Times cited : (51)

References (46)
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    • For the asymmetric synthesis of 1-substituted tetrahydroisoquinolines see, for example: (a) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1986, 23, 395-398. (b) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (c) Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc. 1889, 111, 4859-4863. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 90-102. (e) Kang, J.; Kim, J. B.; Cho, K. H.; Cho, B. T. Tetrahedron: Asymmetry 1997, 8, 657- 660. (f) Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607-4610. (g) Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712. (h) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1896, 7, 53-56. (i) Pyne, S. G.; Hajipour, A. R. Tetrahedron 1992, 48, 9385-9390. (j) Murahashi, S.; Sun, J.; Tsuda, T. Tetrahedron Lett. 1993, 34, 2645-2648.
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    • For the asymmetric synthesis of 1-substituted tetrahydroisoquinolines see, for example: (a) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1986, 23, 395-398. (b) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (c) Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc. 1889, 111, 4859-4863. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 90-102. (e) Kang, J.; Kim, J. B.; Cho, K. H.; Cho, B. T. Tetrahedron: Asymmetry 1997, 8, 657- 660. (f) Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607- 4610. (g) Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712. (h) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1896, 7, 53-56. (i) Pyne, S. G.; Hajipour, A. R. Tetrahedron 1992, 48, 9385-9390. (j) Murahashi, S.; Sun, J.; Tsuda, T. Tetrahedron Lett. 1993, 34, 2645-2648.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6709-6712
    • Suzuki, H.1    Aoyagi, S.2    Kibayashi, C.3
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    • For the asymmetric synthesis of 1-substituted tetrahydroisoquinolines see, for example: (a) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1986, 23, 395-398. (b) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (c) Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc. 1889, 111, 4859-4863. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 90-102. (e) Kang, J.; Kim, J. B.; Cho, K. H.; Cho, B. T. Tetrahedron: Asymmetry 1997, 8, 657- 660. (f) Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607- 4610. (g) Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712. (h) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1896, 7, 53-56. (i) Pyne, S. G.; Hajipour, A. R. Tetrahedron 1992, 48, 9385-9390. (j) Murahashi, S.; Sun, J.; Tsuda, T. Tetrahedron Lett. 1993, 34, 2645-2648.
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    • For the asymmetric synthesis of 1-substituted tetrahydroisoquinolines see, for example: (a) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1986, 23, 395-398. (b) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (c) Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc. 1889, 111, 4859-4863. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 90-102. (e) Kang, J.; Kim, J. B.; Cho, K. H.; Cho, B. T. Tetrahedron: Asymmetry 1997, 8, 657- 660. (f) Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607- 4610. (g) Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712. (h) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1896, 7, 53-56. (i) Pyne, S. G.; Hajipour, A. R. Tetrahedron 1992, 48, 9385-9390. (j) Murahashi, S.; Sun, J.; Tsuda, T. Tetrahedron Lett. 1993, 34, 2645-2648.
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    • Pyne, S.G.1    Hajipour, A.R.2
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    • 0027511699 scopus 로고
    • For the asymmetric synthesis of 1-substituted tetrahydroisoquinolines see, for example: (a) Kano, S.; Yuasa, Y.; Shibuya, S. Heterocycles 1986, 23, 395-398. (b) Chan, W.; Lee, A. W. M.; Jiang, L. Tetrahedron Lett. 1995, 36, 715-718. (c) Polniaszek, R. P.; Kaufman, C. R. J. Am. Chem. Soc. 1889, 111, 4859-4863. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 90-102. (e) Kang, J.; Kim, J. B.; Cho, K. H.; Cho, B. T. Tetrahedron: Asymmetry 1997, 8, 657- 660. (f) Munchoff, M. J.; Meyers, A. I. J. Org. Chem. 1996, 61, 4607- 4610. (g) Suzuki, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1995, 36, 6709-6712. (h) Ukaji, Y.; Kenmoku, Y.; Inomata, K. Tetrahedron: Asymmetry 1896, 7, 53-56. (i) Pyne, S. G.; Hajipour, A. R. Tetrahedron 1992, 48, 9385-9390. (j) Murahashi, S.; Sun, J.; Tsuda, T. Tetrahedron Lett. 1993, 34, 2645-2648.
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    • Isoquinolines
    • Grethe, G., Ed.; Wiley: New York
    • See, for example: (a) Dyke, S. F.; Kinsman, R. G. Kametami, T. G.; Fokumato, K.; McDonald, E. Isoquinolines. In Heterocyclic Compounds; Grethe, G., Ed.; Wiley: New York, 1981; Vol. 38, pp 1-275. (b) Meyers, A. I. Tetrahedron 1998, 48, 2589-2612.
    • (1981) Heterocyclic Compounds , vol.38 , pp. 1-275
    • Dyke, S.F.1    Kinsman, R.G.2    Kametami, T.G.3    Fokumato, K.4    McDonald, E.5
  • 13
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    • See, for example: (a) Dyke, S. F.; Kinsman, R. G. Kametami, T. G.; Fokumato, K.; McDonald, E. Isoquinolines. In Heterocyclic Compounds; Grethe, G., Ed.; Wiley: New York, 1981; Vol. 38, pp 1-275. (b) Meyers, A. I. Tetrahedron 1998, 48, 2589-2612.
    • (1998) Tetrahedron , vol.48 , pp. 2589-2612
    • Meyers, A.I.1
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    • note
    • 3)].
  • 34
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    • For the influence of LiCl on the reactivity of metal enolates, see: (a) Miller, S. A.; Griffiths, S. L.; Seebach D. Helv. Chim. Acta 1993, 76, 563-571. (b) Bossler, H. G.; Seebach, D. Helv. Chim. Acta 1994, 77, 1124-1129.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 563-571
    • Miller, S.A.1    Griffiths, S.L.2    Seebach, D.3
  • 35
    • 0000398245 scopus 로고
    • For the influence of LiCl on the reactivity of metal enolates, see: (a) Miller, S. A.; Griffiths, S. L.; Seebach D. Helv. Chim. Acta 1993, 76, 563-571. (b) Bossler, H. G.; Seebach, D. Helv. Chim. Acta 1994, 77, 1124-1129.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 1124-1129
    • Bossler, H.G.1    Seebach, D.2
  • 36
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    • The anti/syn nomenclature used makes reference to the relative positions of both benzylic protons in the 1,2-diarylethylamine skeleton when the carbon chain is drawn in a way in which both aryl groups are placed with the less steric repulsions between each other. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. 1985, 97, 1-12.
    • (1985) Angew. Chem. , vol.97 , pp. 1-12
    • Masamune, S.1    Choy, W.2    Petersen, J.S.3    Sita, L.R.4
  • 40
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    • For a recent review on Pictet-Spengler cyclization, see: Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842.
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2


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