Atropisomeric benzamides and naphthamides as chiral auxiliaries

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 19, 2000, Pages 3232-3249

  Clayden, Jonathan ^a   Helliwell, Madeleine ^a   McCarthy, Catherine ^a   Westlund, Neil ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; DERIVATIVES; ELECTRONS; ESTERS; ISOMERS; STEREOCHEMISTRY;

CHIRAL AUXILIARIES;

AROMATIC COMPOUNDS;

EID: 0034619274     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b004682p     Document Type: Article

References (76)

1. J. Clayden, Synlett, 1998, 810.
2. J. Clayden, Angew. Chem., Int. Ed. Engl., 1997, 36, 949.
3. P. Bowles, J. Clayden and M. Tomkinson, Tetrahedron Lett., 1995, 36, 9219.
4. P. Bowles, J. Clayden, M. Helliwell, C. McCarthy, M. Tomkinson and N. Westlund, J. Chem. Soc., Perkin Trans, 1, 1997, 2607.
5. J. Clayden, N. Westlund and F. X. Wilson, Tetrahedron Lett., 1996, 37, 5577.
6. J. Clayden, N. Westlund, R. L. Beddoes and M. Helliwell, J. Chem. Soc., Perkin Trans, 1, 2000, 1351.
7. J. Clayden, C. McCarthy, N. Westlund and C. S. Frampton, J. Chem. Soc., Perkin Trans, 1, 2000, 1363.
8. J. Clayden, N. Westlund and C. S. Frampton, J. Chem. Soc., Perkin Trans. 1, 2000, 1379.
9. J. Clayden and J. H. Pink, Tetrahedron Lett., 1997, 38, 2561.
10. J. Clayden, M. Darbyshire, J. H. Pink, N. Westlund and F. X. Wilson, Tetrahedron Lett., 1997, 38, 8487.
11. J. Clayden, N. Westlund and F. X. Wilson, Tetrahedron Lett., 1999, 40, 3329.
12. J. Clayden and L. W. Lai, Angew. Chem., Int. Ed., 1999, 38, 2556.
13. J. Clayden, P. Johnson, J. H. Pink and M. Helliwell, J. Org. Chem., 2000, in press.
14. Preliminary communication: J. Clayden, C. McCarthy and J. G. Gumming, Tetrahedron Lett., 2000, 41, 3279.
15. J. Clayden, C. McCarthy and J. G. Gumming, Tetrahedron: Asymmetry, 1998, 9, 1427.
16. R. Noyori, Asymmetrie Catalysis in Organic Synthesis, Wiley, New York, 1994.
17. C. Bolm and K. Muniz, Chem. Soc, Rev., 1999, 28, 51.
18. E. P. Kündig, D. Amurrio, G. Anderson, D. Beruhen, K. Khan, A. Ripa and L. Ronggang, Pure Appl. Chem., 1997, 69, 543.
19. S. G. Davies, Pure Appl. Chem., 1988, 60, 13.
20. Y. le and G. Fu, Chem. Commun., 2000, 119.
21. C. H. Heathcock and M. C. Pirrung, J. Org. Chem., 1980, 45, 1727.
22. C. H. Heathcock, M. C. Pirrung, S. H. Montgomery and J. Lampe, Tetrahedron, 1981, 37, 4087.
23. P. A. Bartlett and C. P. Holmes, Tetrahedron Lett., 1983, 24, 1365.
24. N. K. Kochetkov, D. V. Yashunskii, A. F. Sviridov and M. S. Ermolenko, Carbohydr. Res., 1990, 200, 209.
25. R. D. Walkup and Y. S. Kim, Tetrahedron Lett., 1995, 36, 3091.
26. S. Hoagland, Y. Morita, D. L. Bai, H. P. Maerki, K. Kees, L. Brown and C. H. Heathcock, J. Org. Chem., 1988, 53, 4730.
27. Y. Kobayashi, H. Uchiyama, H. Kanbara and F. Sato, J. Am. Chem. Soc., 1985, 107, 5541.
28. C. H. Heathcock, B. L. Finkelstein, E. T. Jarvi, P. A. Radel and C. R. Hadley, J. Org. Chem., 1988, 53, 1922.
29. M. Kusakabe and F. Sato, J. Org. Chem., 1989, 54, 3486.
30. M. Braun, S. Mross and I. Schwarz, Synthesis, 1998, 83.
31. M. Ahn, K. Tanaka and K. Fuji, J. Chem. Soc., Perkin Trans, 1, 1998, 185.
32. A. D. Hughes and N. S. Simpkins, Synlett, 1998, 967.
33. A. D. Hughes, D. A. Price and N. S. Simpkins, J. Chem. Soc., Perkin Trans. 7, 1999, 1295.
34. O. Kitagawa, H. Izawa, K. Sato, A. Dobashi and T. Taguchi, J. Org. Chem., 1998, 63, 2634.
35. O. Kitagawa, S.-i. Momose, Y. Fushimi and T. Taguchi, Tetrahedron Lett., 1999, 40, 8827.
36. A. D. Hughes, D. A. Price, O. Shishkin and N. S. Simpkins, Tetrahedron Lett., 1996, 37, 7607.
37. H. Koide and M. Uemura, Chem. Commun., 1998, 2483.
38. J. A. J. M. Vekemans, J. A. F. Boogers and H. M. Buck, J. Org. Chem., 1991, 56, 10.
39. Y. Ikeura, Y. Ishichi, T. Tanaka, A. Fujishima, M. Murabayashi, M. Kawada, T. Ishimaru, I. Kamo, T. Doi and H. Natsugari, J. Med. Chem., 1998, 41, 4232.
40. M. P. Sibi and V. Snieckus, J. Org. Chem., 1983, 48, 1935.
41. A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy, J. H. Pink, N. .Westlund and S. A. Yasin, Tetrahedron, 1998, 54, 13277.
42. J. Clayden, C. S. Frampton, C. McCarthy and N. Westlund, Tetrahedron, 1999, 55, 14161.
43. J. J. Court and D. J. Hlasta, Tetrahedron Lett., 1996, 37, 1335.
44. J. Clayden, J. H. Pink and S. A. Yasin, Tetrahedron Lett., 1998, 39, 105.
45. R. J. Mills, N. J. Taylor and V. Snieckus, J. Org. Chem., 1989, 54, 4372.
46. D. R. Anderson, N. C. Faibish and P. Beak, J. Am. Chem. Soc., 1999, 121, 7553.
47. D. Hoppe, M. Paetow and F. Hintze, Angew. Client., Int. Ed. Engl., 1993, 32, 394.
48. J. Clayden, J. H. Pink, N. Westlund and F. X. Wilson, Tetrahedron Leu., 1998, 39, 8377.
49. Y. Giundon, C. Yoakim and H. E. Morton, Tetrahedron Lett., 1983, 24, 2969.
50. M. E. Jung and M. A. Lyster, J. Org. Chem., 1977, 42, 3761.
51. R. J. Mills, R. F. Horvath, M. P. Sibi and V. Snieckus, Tetrahedron Lett., 1985, 26, 1145.
52. For other examples of C-C bonded chiral auxiliaries, see Y. Watanabe, Y. Ono, S. Hayashi, Y. Ueno and T. Toru, J. Chem. Soc., Perkin Trans. 1, 1996, 1879;
53. R. L. Funk and G. Yang, Tetrahedron Lett., 1999, 40, 1073.
54. M. T. Reetz, M. W. Drewes and A. Schmilz, Angew. Chem., Int. Ed. Engl., 1987, 26, 1141.
55. M. Reetz, Angew. Chem., Int. Ed. Engl., 1991, 30, 1531.
56. M. T. Reetz, K. Rölfing and N. Griebenow, Tetrahedron Lett., 1994, 35, 1969.
57. C. Beaulieu and C. Spino, Tetrahedron Lett., 1999, 40, 1637.
58. C. Spino and C. Beaulieu, J. Am. Chem. Soc., 1998, 120, 11832.
59. I. Savage, E. J. Thomas and P. D. Wilson, J. Chem. Soc., Perkin Trans, 1, 1999, 3291.
60. H. Imogaï, Y. Petit and M. Larchevêque. Synlett, 1997, 615.
61. J. Clayden, C. McCarthy and M. Helliwell, Chem. Commun., 1999, 2059.
62. M. T. Reetz, Angew. Chem., Int. Ed. Engl, 1984, 23, 556.
63. A. Alexakis, P. Mangeney, N. Lensen, J. Tranchier, R. Gosmini and S. Raussou, Pure Appl. Chem., 1996, 68, 531.
64. M. Asami, H. Ohno, S. Kobayashi and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1978, 51, 1869.
65. T. Mukaiyama, Y. Sakito and M. Asami, Chem. Lett., 1978, 1253.
66. Bringmann has made extensive use of a conceptually similar atroposelective dynamic resolution for the synthesis of enantiomerically pure biaryls: see G. Bringmann, M. Breuning, S. Tasler, H. Endress, C. L. J. Ewers, L. Göbel, K. Peters and E.-M. Peters, Chem. Eur. J., 1999, 5, 3029 and references therein.
67. S. Thayumanavan, A. Basu and P. Beak, J. Am. Chem. Soc., 1997, 119, 8209.
68. J. Clayden and L. W. Lai, unpublished results.
69. W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Brocksom, T.-t. Li, D. J. Faulkner and M. R. Petersen, J. Am. Chem. Soc., 1970, 92, 741.
70. A. E. Wick, D. Felix, K. Steen and A. Eschenmoser, Helv. Chim. Acta, 1964, 47, 2425.
71. J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969, 34, 2543.
72. R. K. Hill, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1985, vol. 3, p. 503.
73. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
74. M. Julia, V. Pfeuty-Saint Jalmes, K. Pie, J.-N. Verpeaux and G. Hollingworth, Bull. Soc. Chim. Fr., 1996, 133, 15.
75. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation (1985 and 1992).
76. SHELXS86: G. M. Sheldrick, in Crystallographic Computing 3, ed. G. M. Sheldrick, C. Krueger and R. Goddard, OUP, Oxford, 1985, pp. 175-189.