Novel concepts in directed biaryl synthesis, 80([≠]). - Synthesis of axially chiral biaryls by atropo-diastereoselective cleavage of configurationally unstable biaryl lactones with menthol-derived O- nucleophiles

European Journal of Organic Chemistry

Volumn , Issue 11, 1999, Pages 3047-3055

  Bringmann, Gerhard ^a   Breuning, Matthias ^a   Walter, Rainer ^a   Wuzik, Andreas ^a   Peters, Karl ^b   Peters, Eva Maria ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b MAX PLANCK INSTITUT FÜR FESTKÖRPERFORSCHUNG   (Germany)

Author keywords

Asymmetric synthesis; Atropisomerism; Axial chirality; Biaryls; Dynamic kinetic resolution

Indexed keywords

LACTONE; MENTHOL;

ARTICLE; CATALYSIS; CHIRALITY; CRYSTALLIZATION; DNA CLEAVAGE; DRUG SYNTHESIS; ENANTIOMER; LIGAND BINDING; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032727557     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<3047::aid-ejoc3047>3.0.co;2-o     Document Type: Article

References (58)

1. [1a] C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503-517.
2. [1b] L. Pu, Chem. Rev. 1998, 98, 2405-2494.
3. Reviews: [2a] G. Bringmann, C. Günther, M. Ochse, O. Schupp, S. Tasler in Prog. Chem. Org. Nat. Prod. (Eds.: W. Herz, H. Falk, G. W. Kirby, R. E. Moore, C. Tamm), submitted.
4. [2b] G. Bringmann, F. Pokorny in The Alkaloids, vol. 46 (Ed.: G. A. Cordell), Academic Press, New York, 1995, pp. 127-271.
5. [2c] G. Bringmann, G. François, L. Aké Assí, J. Schlauer, Chimia 1998, 52, 18-28.
6. [2d] G. Bringmann, Bull Soc. Chim. Belg. 1996, 105, 601-613.
7. Reviews: [3a] K. B. G. Torssell, Natural Product Chemistry, Taylor and Francis, New York, 1997.
8. [3b] T. Okuda, T. Yoshida, T. Hatano in Prog. Chem. Org. Nat. Prod., vol. 66 (Eds.: W. Herz, G. W. Kirby, R. E. Moore, W. Steglich, C. Tamm), Springer, Vienna, 1995, pp. 1-117.
9. [3c] M. A. Rizzacasa in Studies in Natural Product Chemistry, vol. 20, Part F (Ed.: Attaur-Rahman), Elsevier, Amsterdam, 1998, pp. 407-455.
10. G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525-558.
11. [5a] G. Bringmann, S. Tasler in Current Trends in Organic Synthesis (Eds.: C. Scolastico, F. Nicotra), Plenum Publishing Corporation, New York, 1999, pp. 105-116.
12. [5b] G. Bringmann, O. Schupp, S. Afr. J. Chem. 1994, 47, 83-102.
13. G. Bringmann, M. Breuning, Tetrahedron: Asymmetry 1998, 9, 667-679.
14. [7a] T. R. Govindachari, P. C. Parthasarathy, Tetrahedron 1971, 27, 1013-1026.
15. [7b] T. R. Govindachari, P. C. Parthasarathy, T. G. Rajagopalan, H. K. Desai, K. S. Ramachandran, E. Lee, J. Chem. Soc., Perkin Trans. 1 1975, 2134-2136.
16. [8a] G. Bringmann, H. Reuscher, Tetrahedron Lett. 1989, 30, 5249-5252.
17. [8b] G. Bringmann, H. Reuscher, Angew. Chem. 1989, 101, 1725-1726; Angew. Chem. Int. Ed. Engl. 1989, 28, 1672-1673.
18. [8b] G. Bringmann, H. Reuscher, Angew. Chem. 1989, 101, 1725-1726; Angew. Chem. Int. Ed. Engl. 1989, 28, 1672-1673.
19. [9a] M. A. Rizzacasa, M. V. Sargent, J. Chem. Soc., Chem. Commun. 1989, 301-302.
20. [9b] M. A. Rizzacasa, M. V. Sargent, J. Chem. Soc, Perkin Trans. 1 1991, 845-854.
21. G. Bringmann, T. Hartung, L. Göbel, O. Schupp, C. L. J. Ewers, B. Schöner, R. Zagst, K. Peters, H. G. von Schnering, C. Burschka, Liebigs Ann. Chem. 1992, 225-232.
22. [18] and: [11a] D. I. Davies, C. Waring, J. Chem. Soc. C 1967, 1639-1642.
23. [11b] O. deFrutos, A. M. Echavarren, Tetrahedron Lett. 1996, 37, 8953-8956.
24. For the now recommended (M)/(P) notation for axial chirality, see: G. Helmchen in Methods of Organic Chemistry (Houben-Weyl), 4th ed., vol. E21a (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, pp. 11-13.
25. [12] the stereochemically analogous biaryls with R = Me ("a series") and R = OMe ("b series") have different stereodescriptors at the biaryl axis.
26. [14a] G. Bringmann, T. Hartung, Synthesis 1992, 433-435.
27. [14b] G. Bringmann, T. Hartung, Angew. Chem. 1992, 104, 782-783; Angew. Chem. Int. Ed. Engl. 1992, 31, 761-762.
28. [14b] G. Bringmann, T. Hartung, Angew. Chem. 1992, 104, 782-783; Angew. Chem. Int. Ed. Engl. 1992, 31, 761-762.
29. [14c] G. Bringmann, T. Hartung, Tetrahedron 1993, 49, 7891-7902.
30. [14d] G. Bringmann, M. Breuning, Tetrahedron: Asymmetry 1999, 10, 385-390.
31. [15a] D. Seebach, G. Jaeschke, K. Gottwald, K. Matsuda, R. Formisano, D. A. Chaplin, M. Breuning, G. Bringmann, Tetrahedron 1997, 53, 7539-7556.
32. [15b] G. Bringmann, T. Pabst, S. Busemann, K. Peters, E.-M. Peters, Tetrahedron 1998, 54, 1425-1438.
33. G. Bringmann, M. Breuning, S. Tasler, H. Endress, C. L. J. Ewers, L. Göbel, K. Peters, E.-M. Peters, Chem. Eur. J., 1999, in press.
34. G. Bringmann, R. Walter, C. L. J. Ewers, Synlett 1991, 581-583.
35. W. Wang, V. Snieckus, J. Org. Chem. 1992, 57, 424-426.
36. Reviews: [19a] S. P. Stanforth, Tetrahedron 1998, 54, 263-303.
37. [19b] G. Bringmann, R. Walter, R. Weirich, Angew. Chem. 1990, 102, 1006-1019; Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991.
38. [19b] G. Bringmann, R. Walter, R. Weirich, Angew. Chem. 1990, 102, 1006-1019; Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991.
39. [19c] G. Bringmann, R. Walter, R. Weirich in Methods of Organic Chemistry (Houben Weyl), 4th ed., vol. E21a (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, pp. 567-587.
40. [20a] T. G. Gant, A. I. Meyers, Tetrahedron 1994, 50, 2297-2360.
41. [20b] K. S. Feldman, R. S. Smith, J. Org. Chem. 1996, 61, 2606-2612.
42. [20c] K. Kamikawa, T. Watanabe, M. Uemura, J. Org. Chem. 1996, 1375-1384.
43. [20d] B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 106, 1962-1964; Angew. Chem. Int. Ed. Engl. 1994, 33, 1842-1844.
44. [20d] B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 106, 1962-1964; Angew. Chem. Int. Ed. Engl. 1994, 33, 1842-1844.
45. [20e] G.-Q. Lin, M. Zhong, Tetrahedron: Asymmetry 1997, 8, 1369-1372.
46. [20f] T. Sugimura, H. Yamada, S. Inoue, A. Tai, Tetrahedron: Asymmetry 1997, 8, 649-655.
47. [20g] S. Miyano, H. Fukushima, S. Handa, H. Ito, H. Hashimoto, Bull. Chem. Soc. Jpn. 1988, 61, 3249-3254.
48. [20h] V. H. Rawal, A. S. Florjancic, S. P. Singh, Tetrahedron Lett. 1994, 35, 8985-8988.
49. E. J. Corey, H. E. Ensley, J. Am. Chem. Soc. 1975, 97, 6908-6909.
50. G. Bringmann, W. Saeb, M. Rübenacker, Tetrahedron 1999, 55, 423-432.
51. G. Bringmann, M. Breuning, Tetrahedron: Asymmetry 1998, 9, 667-679.
52. [14]
53. [12] the stereo-descriptor at the biaryl axis changes from (P) to (M).
54. G. Bringmann, A. Wuzik, M. Breuning, P. Henschel, E.-M. Peters, K. Peters, Tetrahedron Asymmetry, 1999, 10, 3025-3031.
55. V. P. Fedulov, E. M. Glazunova, V. I. Nicitin, Khim. Tadzh. 1973, 35-40 [Chem. Abstr. 1976, 84, 73791c].
56. V. P. Fedulov, E. M. Glazunova, V. I. Nicitin, Khim. Tadzh. 1973, 35-40 [Chem. Abstr. 1976, 84, 73791c].
57. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-117637 and -116638. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/ 336-033; E-mail: deposit@ccdc.cam.ac.uk].
58. G. M. Sheldrick, Program Package SHELXTL-PLUS, Release 4.1, Siemens Analytical Instruments Inc., Madison, WI 53719, USA, 1990.