Catalytic asymmetric synthesis of polysubstituted cyclohexa-1,3-dienes from β-branched α,β-alkenals

Russian Chemical Bulletin

Volumn 45, Issue 3, 1996, Pages 623-629

  Nigmatov, A G ^a   Serebryakov, E P ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

(S) prolinol; Chiral 1 amino 1,3 dienes, generation and in situ transformation; Chiral cyclohexa 1,3 dienes and hexahydronaphthalenes, synthesis; Monoalkylidene malonates; 4+2 cycloaddition, stereoselectivity

Indexed keywords

EID: 0043286601     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01435793     Document Type: Article

References (59)

1. L. A. Paquette, Asymmetric Synthesis / Ed. J. D. Morrison, Academic Press, New York - Orlando, FLA, 1984, 3(B), 455; W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876; G. Helmchen, R. Karge, and J. Weetman, Modern Synthetic Methods 1986 / Ed. R. Sheffold, Springer, New York, 1986, 4, 262; Tetrahedron Organic Chemistry Series, 8 / Ed. W. Carruthers, Pergamon, Oxford, UK, 1990, 61; E. J. Thomas, Acc. Chem. Res., 1991, 24, 229; K. Krohn, Organic Synthesis Highlights 1991, VCH, Weinheim, FRG, 1991, 54.
2. L. A. Paquette, Asymmetric Synthesis / Ed. J. D. Morrison, Academic Press, New York - Orlando, FLA, 1984, 3(B), 455; W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876; G. Helmchen, R. Karge, and J. Weetman, Modern Synthetic Methods 1986 / Ed. R. Sheffold, Springer, New York, 1986, 4, 262; Tetrahedron Organic Chemistry Series, 8 / Ed. W. Carruthers, Pergamon, Oxford, UK, 1990, 61; E. J. Thomas, Acc. Chem. Res., 1991, 24, 229; K. Krohn, Organic Synthesis Highlights 1991, VCH, Weinheim, FRG, 1991, 54.
3. L. A. Paquette, Asymmetric Synthesis / Ed. J. D. Morrison, Academic Press, New York - Orlando, FLA, 1984, 3(B), 455; W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876; G. Helmchen, R. Karge, and J. Weetman, Modern Synthetic Methods 1986 / Ed. R. Sheffold, Springer, New York, 1986, 4, 262; Tetrahedron Organic Chemistry Series, 8 / Ed. W. Carruthers, Pergamon, Oxford, UK, 1990, 61; E. J. Thomas, Acc. Chem. Res., 1991, 24, 229; K. Krohn, Organic Synthesis Highlights 1991, VCH, Weinheim, FRG, 1991, 54.
4. L. A. Paquette, Asymmetric Synthesis / Ed. J. D. Morrison, Academic Press, New York - Orlando, FLA, 1984, 3(B), 455; W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876; G. Helmchen, R. Karge, and J. Weetman, Modern Synthetic Methods 1986 / Ed. R. Sheffold, Springer, New York, 1986, 4, 262; Tetrahedron Organic Chemistry Series, 8 / Ed. W. Carruthers, Pergamon, Oxford, UK, 1990, 61; E. J. Thomas, Acc. Chem. Res., 1991, 24, 229; K. Krohn, Organic Synthesis Highlights 1991, VCH, Weinheim, FRG, 1991, 54.
5. L. A. Paquette, Asymmetric Synthesis / Ed. J. D. Morrison, Academic Press, New York - Orlando, FLA, 1984, 3(B), 455; W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876; G. Helmchen, R. Karge, and J. Weetman, Modern Synthetic Methods 1986 / Ed. R. Sheffold, Springer, New York, 1986, 4, 262; Tetrahedron Organic Chemistry Series, 8 / Ed. W. Carruthers, Pergamon, Oxford, UK, 1990, 61; E. J. Thomas, Acc. Chem. Res., 1991, 24, 229; K. Krohn, Organic Synthesis Highlights 1991, VCH, Weinheim, FRG, 1991, 54.
6. L. A. Paquette, Asymmetric Synthesis / Ed. J. D. Morrison, Academic Press, New York - Orlando, FLA, 1984, 3(B), 455; W. Oppolzer, Angew. Chem., Int. Ed. Engl., 1984, 23, 876; G. Helmchen, R. Karge, and J. Weetman, Modern Synthetic Methods 1986 / Ed. R. Sheffold, Springer, New York, 1986, 4, 262; Tetrahedron Organic Chemistry Series, 8 / Ed. W. Carruthers, Pergamon, Oxford, UK, 1990, 61; E. J. Thomas, Acc. Chem. Res., 1991, 24, 229; K. Krohn, Organic Synthesis Highlights 1991, VCH, Weinheim, FRG, 1991, 54.
7. H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; K. Mikami, M. Terada, S. Narisawa, and T. Nakai, SYNLETT, 1992, 255.
8. H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; K. Mikami, M. Terada, S. Narisawa, and T. Nakai, SYNLETT, 1992, 255.
9. A. G. Fallis and Y. F. Lu, Adv. Cycloaddition, 1993, 3, 1.
10. E. Winterfeldt, Chem. Rev., 1993, 93, 827.
11. B. M. Trost, S. A. Godleski, and J. P. Genēt, J. Am. Chem. Soc., 1978, 100, 3930; B. M. Trost, D. O'Krongly, and J. L. Belletire, J. Am. Chem. Soc., 1980, 102, 7595.
12. B. M. Trost, S. A. Godleski, and J. P. Genēt, J. Am. Chem. Soc., 1978, 100, 3930; B. M. Trost, D. O'Krongly, and J. L. Belletire, J. Am. Chem. Soc., 1980, 102, 7595.
13. C. Siegel and E. R. Thornton, Tetrahedron Lett., 1989, 29, 5225.
14. R. Tripathy, P. J. Carroll, and E. R. Thornton, J. Am. Chem. Soc., 1991, 113, 7630; C. Siegel and E. R. Thornton, Tetrahedron: Asymmetry, 1991, 2, 1413.
15. R. Tripathy, P. J. Carroll, and E. R. Thornton, J. Am. Chem. Soc., 1991, 113, 7630; C. Siegel and E. R. Thornton, Tetrahedron: Asymmetry, 1991, 2, 1413.
16. S. David, J. Eustache, and A. Lubineau, J. Chem. Soc., Perkin Trans. 1, 1976, 2274; S. David, A. Lubineau, and A. Thieffry, Tetrahedron, 1978, 34, 299; A. David, A. Lubineau, and J. M. Vatèle, J. Chem. Soc., Chem. Commun., 1978, 535; R. M. Giuliano J. H. Buzby, J. H. Macropulos, and J. P. Springer, J. Org. Chem., 1990, 55, 3555.
17. S. David, J. Eustache, and A. Lubineau, J. Chem. Soc., Perkin Trans. 1, 1976, 2274; S. David, A. Lubineau, and A. Thieffry, Tetrahedron, 1978, 34, 299; A. David, A. Lubineau, and J. M. Vatèle, J. Chem. Soc., Chem. Commun., 1978, 535; R. M. Giuliano J. H. Buzby, J. H. Macropulos, and J. P. Springer, J. Org. Chem., 1990, 55, 3555.
18. S. David, J. Eustache, and A. Lubineau, J. Chem. Soc., Perkin Trans. 1, 1976, 2274; S. David, A. Lubineau, and A. Thieffry, Tetrahedron, 1978, 34, 299; A. David, A. Lubineau, and J. M. Vatèle, J. Chem. Soc., Chem. Commun., 1978, 535; R. M. Giuliano J. H. Buzby, J. H. Macropulos, and J. P. Springer, J. Org. Chem., 1990, 55, 3555.
19. S. David, J. Eustache, and A. Lubineau, J. Chem. Soc., Perkin Trans. 1, 1976, 2274; S. David, A. Lubineau, and A. Thieffry, Tetrahedron, 1978, 34, 299; A. David, A. Lubineau, and J. M. Vatèle, J. Chem. Soc., Chem. Commun., 1978, 535; R. M. Giuliano J. H. Buzby, J. H. Macropulos, and J. P. Springer, J. Org. Chem., 1990, 55, 3555.
20. A. P. Kozikowski, T. R. Nieduzak, T. Konoike, and J. P. Springer, J. Am. Chem. Soc., 1987, 109, 5167; P. G. McDougal, J. M. Jump, C. Rojas, and J. D. Rico, Tetrahedron Lett., 1989, 30, 3897; T. Hamada, T. Zenkoh, H. Sato, and O. Yonemitsu, Tetrahedron Lett., 1991, 32, 1649.
21. A. P. Kozikowski, T. R. Nieduzak, T. Konoike, and J. P. Springer, J. Am. Chem. Soc., 1987, 109, 5167; P. G. McDougal, J. M. Jump, C. Rojas, and J. D. Rico, Tetrahedron Lett., 1989, 30, 3897; T. Hamada, T. Zenkoh, H. Sato, and O. Yonemitsu, Tetrahedron Lett., 1991, 32, 1649.
22. A. P. Kozikowski, T. R. Nieduzak, T. Konoike, and J. P. Springer, J. Am. Chem. Soc., 1987, 109, 5167; P. G. McDougal, J. M. Jump, C. Rojas, and J. D. Rico, Tetrahedron Lett., 1989, 30, 3897; T. Hamada, T. Zenkoh, H. Sato, and O. Yonemitsu, Tetrahedron Lett., 1991, 32, 1649.
23. R. Bloch and N. Chaptal-Gradoz, Tetrahedron Lett., 1992, 33, 6147; P. A. Brown, R. V. Bonnert, R. P. Jenkins, N. J. Lawrence, and M. R. Selim, J. Chem. Soc., Perkin Trans. I, 1991, 1892; S. Hatakeyama, K. Sugawahara, M. Kawamura, and S. Takano, Tetrahedron Lett., 1991, 32, 4509.
24. R. Bloch and N. Chaptal-Gradoz, Tetrahedron Lett., 1992, 33, 6147; P. A. Brown, R. V. Bonnert, R. P. Jenkins, N. J. Lawrence, and M. R. Selim, J. Chem. Soc., Perkin Trans. I, 1991, 1892; S. Hatakeyama, K. Sugawahara, M. Kawamura, and S. Takano, Tetrahedron Lett., 1991, 32, 4509.
25. R. Bloch and N. Chaptal-Gradoz, Tetrahedron Lett., 1992, 33, 6147; P. A. Brown, R. V. Bonnert, R. P. Jenkins, N. J. Lawrence, and M. R. Selim, J. Chem. Soc., Perkin Trans. I, 1991, 1892; S. Hatakeyama, K. Sugawahara, M. Kawamura, and S. Takano, Tetrahedron Lett., 1991, 32, 4509.
26. M. C. Carreño, M. B. Cid, F. Colobert, J. L. Garcia Ruano, and G. Solladié, Tetrahedron: Asymmetry, 1994, 5, 1439.
27. H. Adams, D. Neville Jones, M. C. Aversa, P. Bonaccorsi, and P. Giannetto, Tetrahedron Lett., 1993, 34, 6481; P. Gosselin, E. Bonfand, P. Hayes, R. Retoux, and C. Maignan, Tetrahedron: Asymmetry, 1994, 5, 781; M. C. Aversa, P. Bonaccorsi, P. Gianetto, and D. Neville Jones, Tetrahedron: Asymmetry, 1994, 5, 805.
28. H. Adams, D. Neville Jones, M. C. Aversa, P. Bonaccorsi, and P. Giannetto, Tetrahedron Lett., 1993, 34, 6481; P. Gosselin, E. Bonfand, P. Hayes, R. Retoux, and C. Maignan, Tetrahedron: Asymmetry, 1994, 5, 781; M. C. Aversa, P. Bonaccorsi, P. Gianetto, and D. Neville Jones, Tetrahedron: Asymmetry, 1994, 5, 805.
29. H. Adams, D. Neville Jones, M. C. Aversa, P. Bonaccorsi, and P. Giannetto, Tetrahedron Lett., 1993, 34, 6481; P. Gosselin, E. Bonfand, P. Hayes, R. Retoux, and C. Maignan, Tetrahedron: Asymmetry, 1994, 5, 781; M. C. Aversa, P. Bonaccorsi, P. Gianetto, and D. Neville Jones, Tetrahedron: Asymmetry, 1994, 5, 805.
30. R. Beaudegnies and L. Ghosez, Tetrahedron: Asymmetry, 1994, 5, 557.
31. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, An. Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403; R. H. Schlessinger, T. R. R. Pettus, J. P. Springer, and K. Hoogsteen, J. Org. Chem., 1994, 59, 3246; R. H. Schlessinger, X.-H. Wu, and T. R. R. Pettus, SYNLETT, 1995, 536.
32. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, An. Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403; R. H. Schlessinger, T. R. R. Pettus, J. P. Springer, and K. Hoogsteen, J. Org. Chem., 1994, 59, 3246; R. H. Schlessinger, X.-H. Wu, and T. R. R. Pettus, SYNLETT, 1995, 536.
33. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, An. Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403; R. H. Schlessinger, T. R. R. Pettus, J. P. Springer, and K. Hoogsteen, J. Org. Chem., 1994, 59, 3246; R. H. Schlessinger, X.-H. Wu, and T. R. R. Pettus, SYNLETT, 1995, 536.
34. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, An. Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403; R. H. Schlessinger, T. R. R. Pettus, J. P. Springer, and K. Hoogsteen, J. Org. Chem., 1994, 59, 3246; R. H. Schlessinger, X.-H. Wu, and T. R. R. Pettus, SYNLETT, 1995, 536.
35. D. Enders, O. Meyer, and G. Raabe, Synthesis, 1992, 1242; J. Barluenga, F. Aznar, C. Valdés, and J. A. Martin, An. Quim., 1993, 89, 115; J. Barluenga, F. Aznar, C. Valdés, J. A. Martin, S. Garcia-Grandez, and E. Martin, J. Am. Chem. Soc., 1993, 115, 4403; R. H. Schlessinger, T. R. R. Pettus, J. P. Springer, and K. Hoogsteen, J. Org. Chem., 1994, 59, 3246; R. H. Schlessinger, X.-H. Wu, and T. R. R. Pettus, SYNLETT, 1995, 536.
36. D. Enders, O. Meyer, G. Raabe, and J. Runsink, Synthesis, 1994, 66.
37. K. Krohn, Angew. Chem., Int. Ed. Engl., 1993, 32, 1582.
38. P. W. Hickmott, Tetrahedron, 1984, 40, 2989.
39. R. F. Menezes, C. A. Zezza, J. Sheu, and M. B. Smith, Tetrahedron Lett., 1989, 30, 3295; A. Defoin, J. Pires, and J. Streith, SYNLETT, 1991, 417.
40. R. F. Menezes, C. A. Zezza, J. Sheu, and M. B. Smith, Tetrahedron Lett., 1989, 30, 3295; A. Defoin, J. Pires, and J. Streith, SYNLETT, 1991, 417.
41. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1993, 233 [Russ. Chem. Bull., 1993, 42, 213 (Engl. Transl.)].
42. A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1993, 233 [Russ. Chem. Bull., 1993, 42, 213 (Engl. Transl.)].
43. E. P. Serebryakov and A. G. Nigmatov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 605 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 527 (Engl. Transl.)]; A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1079 (Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 961 (Engl. Transl.)].
44. E. P. Serebryakov and A. G. Nigmatov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 605 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 527 (Engl. Transl.)]; A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1079 (Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 961 (Engl. Transl.)].
45. E. P. Serebryakov and A. G. Nigmatov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 605 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 527 (Engl. Transl.)]; A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1079 (Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 961 (Engl. Transl.)].
46. E. P. Serebryakov and A. G. Nigmatov, Izv. Akad. Nauk SSSR, Ser. Khim., 1990, 605 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1990, 39, 527 (Engl. Transl.)]; A. G. Nigmatov and E. P. Serebryakov, Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1079 (Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 961 (Engl. Transl.)].
47. A. G. Nigmatov, I. N. Kornilova, and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1996, 154 (Russ. Chem. Bull., 1996, 144 (Engl. Transl.)].
48. A. G. Nigmatov, I. N. Kornilova, and E. P. Serebryakov, Izv. Akad. Nauk, Ser. Khim., 1996, 154 (Russ. Chem. Bull., 1996, 144 (Engl. Transl.)].
49. F. Toda, K. Mori, J. Okada, M. Node, A. Itoh, K. Oomine, and K. Fuji, Chem. Lett., 1988, 131; F. Toda, K. Mori, and A. Satò, Bull. Chem. Soc. Jpn., 1988, 61, 4167.
50. F. Toda, K. Mori, J. Okada, M. Node, A. Itoh, K. Oomine, and K. Fuji, Chem. Lett., 1988, 131; F. Toda, K. Mori, and A. Satò, Bull. Chem. Soc. Jpn., 1988, 61, 4167.
51. O. V. Mikhalev, O. R. Malyshev, M. G. Vinogradov, G. V. Chel'tsova-Bebutova, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1995, 900 [Russ. Chem. Bull., 1995, 44, 873 (Engl. Transl.)].
52. O. V. Mikhalev, O. R. Malyshev, M. G. Vinogradov, G. V. Chel'tsova-Bebutova, and A. V. Ignatenko, Izv. Akad. Nauk, Ser. Khim., 1995, 900 [Russ. Chem. Bull., 1995, 44, 873 (Engl. Transl.)].
53. C. R. Unelius and T. Norin, XVth Conference on Isoprenoids (Zakopane, Poland, Sept. 20-25, 1993). Abstracts of Papers, p. 56.
54. C. Mannich and E. Ganz, Ber., 1922, 55, 3504; C. Mannich and K. Riesert, Ber., 1925, 58, 1116; H. Schenkel and R. Mory, Helv. Chim. Acta, 1950, 33, 16; N. Campbell and R. S. MacPherson, J. Chem. Soc., Perkin Trans. 1, 1974, 43.
55. C. Mannich and E. Ganz, Ber., 1922, 55, 3504; C. Mannich and K. Riesert, Ber., 1925, 58, 1116; H. Schenkel and R. Mory, Helv. Chim. Acta, 1950, 33, 16; N. Campbell and R. S. MacPherson, J. Chem. Soc., Perkin Trans. 1, 1974, 43.
56. C. Mannich and E. Ganz, Ber., 1922, 55, 3504; C. Mannich and K. Riesert, Ber., 1925, 58, 1116; H. Schenkel and R. Mory, Helv. Chim. Acta, 1950, 33, 16; N. Campbell and R. S. MacPherson, J. Chem. Soc., Perkin Trans. 1, 1974, 43.
57. C. Mannich and E. Ganz, Ber., 1922, 55, 3504; C. Mannich and K. Riesert, Ber., 1925, 58, 1116; H. Schenkel and R. Mory, Helv. Chim. Acta, 1950, 33, 16; N. Campbell and R. S. MacPherson, J. Chem. Soc., Perkin Trans. 1, 1974, 43.
58. D. Enders, P. Fey, and H. Kippharat, Org. Prep. Proced. Int., 1985, 17, 1.
59. J. Jacques and C. Fouquey, Tetrahedron Lett., 1971, 4617.