Atropo-diastereoselective cleavage of configurationally unstable biaryl lactones with alkali metal activated primary 1-arylethylamines

Chemistry - A European Journal

Volumn 5, Issue 10, 1999, Pages 3029-3038

  Bringmann, Gerhard ^a   Breuning, Matthias ^a   Tasler, Stefan ^a   Endress, Heike ^a   Ewers, Christian L J ^a   Göbel, Lothar ^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

ETHYLAMINE; LACTONE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHIRALITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032821942     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991001)5:10<3029::AID-CHEM3029>3.0.CO;2-5     Document Type: Article

References (55)

1. Reviews: a) 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;
2. b) K. B. G. Torsseil, Natural Product Chemistry, Taylor and Francis, New York, 1997;
3. c) G. Bringmann, G. François, L. Aké Assi, J. Schlauer, Chimia 1998, 52, 18-28;
4. d) 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, Wien, 1995, pp. 1-117;
5. e) M. A. Rizzacasa in Studies in Natural Product Chemistry, Vol. 20, Part F (Ed.: Atta-ur-Rahman), Elsevier, Amsterdam, 1998, pp. 407-455.
6. a) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadori, Synthesis 1992, 503-517;
7. b) L. Pu, Chem. Rev. 1998, 98, 2405-2494.
8. G. Bringmann, M. Breuning, Tetrahedron: Asymmetry 1998, 9, 667-679.
9. G. Bringmann, M. Breuning, S. Tasler, Synthesis 1999, 525-558.
10. a) G. Bringmann, S. Tasler in Current Trends in Organic Synthesis (Eds.: C. Scolastico, F. Nicotra), Plenum, New York, 1999, pp. 105-116;
11. b) G. Bringmann, O. Schupp, S. Afr. J. Chem. 1994, 47, 83-102.
12. G. Bringmann, W. Saeb, M. Rübenacker, Tetrahedron 1999, 55, 423-432.
13. G. Bringmann, F. Pokorny in The Alkaloids, Vol. 46 (Ed.: G. A. Cordell), Academic Press, New York, 1995, pp. 127-271.
14. 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.
15. For further syntheses of related (albeit sterically less hindered) biaryl lactones, see ref. [22] and: a) D. I. Davies, C. Waring, J. Chem. Soc. (C) 1967, 1639-1642;
16. b) O. deFrutos, A. M. Echavarren, Tetrahedron Lett. 1996, 37, 8953-8956.
17. For the now recommended M/P-denotion 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.
18. G. Bringmann, M. Breuning, R. Walter, A. Wuzik, K. Peters, E.-M. Peters, Eur. J. Org. Chem. 1999, in press.
19. a) D. Seebach, G. Jaeschke, K. Gottwald, K. Matsuda, R. Formisano, D. A. Chaplin, M. Breuning, G. Bringmann, Tetrahedron 1997, 53, 7539-7556;
20. b) G. Bringmann, T. Pabst, S. Busemann, K. Peters, E.-M. Peters, Tetrahedron 1998, 54, 1425-1438.
21. a) G. Bringmann, T. Hartung, Synthesis 1992, 433-435;
22. b) G. Bringmann, T. Härtung, Angew. Chem. 1992, 104, 782-783; Angew. Chem. Int. Ed. Engl. 1992, 31, 761-762;
23. b) G. Bringmann, T. Härtung, Angew. Chem. 1992, 104, 782-783; Angew. Chem. Int. Ed. Engl. 1992, 31, 761-762;
24. c) G. Bringmann, T. Hartung, Tetrahedron 1993, 49, 7891-7902;
25. d) G. Bringmann, M. Breuning, Tetrahedron: Asymmetry 1999, 10, 385-390.
26. a) G. Bringmann, C. L. J. Ewers, L. Göbel, T. Hartung, B. Schöner, O. Schupp, R. Walter in Selective Reactions of Metal-Activated Molecules (Eds.: H. Werner, A. G. Griesbeck, W. Adam, G. Bringmann, W. Kiefer), Vieweg, Braunschweig, 1991, pp. 183-186;
27. b) G. Bringmann, R. Walter, C. L. J. Ewers, Synlett 1991, 581-583.
28. [10]
29. Reviews: a) S. P. Stanforth, Tetrahedron 1998, 54, 263-303;
30. b) G. Bringmann, R. Walter, R. Weirich, Angew. Chem. 1990, 102, 1006-1019; Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991;
31. b) G. Bringmann, R. Walter, R. Weirich, Angew. Chem. 1990, 102, 1006-1019; Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991;
32. c) 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.
33. a) T. G. Gant, A.I. Meyers, Tetrahedron 1994, 50, 2297-2360;
34. b)K. S. Feldman, R. S. Smith, J. Org. Chem. 1996, 61, 2606-2612;
35. c) K. Kamikawa, T. Watanabe, M. Uemura, J. Org. Chem. 1996, 1375-1384;
36. d) B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 706, 1962-1964; Angew. Chem. Int. Ed. Engl. 1994, 33, 1842-1844;
37. d) B. H. Lipshutz, F. Kayser, Z.-P. Liu, Angew. Chem. 1994, 706, 1962-1964; Angew. Chem. Int. Ed. Engl. 1994, 33, 1842-1844;
38. e) G.-Q. Lin, M. Zhong, Tetrahedron: Asymmetry 1997, 8, 1369-1372;
39. f) T. Sugimura, H. Yamada, S. Inoue, A. Tai, Tetrahedron: Asymmetry 1997, 8, 649-655;
40. g) S. Miyano, H. Fukushima, S. Handa, H. Ito, H. Hashimoto, Bull. Chem. Soc. Jpn. 1988, 61, 3249-3254;
41. h) V. H. Rawal, A. S. Florjancic, S. P. Singh, Tetrahedron Lett. 1994, 35, 8985-8988.
42. G. Bringmann, J.-P. Geisler, T. Geuder, G. Künkel, L. Kinzinger, Liebigs Ann. Chem. 1990, 795-805.
43. a) R. R. Rony, J. Am. Chem. Soc. 1969, 97, 6090-6096;
44. b) H. T. Openshaw, N. Whittacker, J. Chem. Soc. (C) 1969, 89-91;
45. c) C. Su, J. W. Watsen, J. Am. Chem. Soc. 1974, 96, 1854-1857.
46. L.-H. Wang, H. Zipse, Liebigs Ann. Chem. 1996, 1501-1509.
47. a) G. Bringmann, T. Hartung, Liebigs Ann. Chem. 1994, 313-316;
48. b) G. Bringmann, M. Breuning, H. Endress, D. Vitt, K. Peters, E.-M. Peters, Tetrahedron 1998, 54, 10677-10690.
49. a) E. H. White, J. Am. Chem. Soc. 1955, 77, 6008-6010;
50. b) S. Miyano, S.-i. Okada, H. Hotta, M. Takeda, T. Suzuki, C. Kabuto, F. Yasuhara, Bull. Chem. Soc. Jpn. 1989, 62, 3886-3891.
51. W. Wang, V. Snieckus, J. Org. Chem. 1992, 57, 424-426.
52. 1H NMR comparison of the atropo-diastereomer (P,R)-22b synthesized independently by reductive amination of the corresponding hydroxy aldehyde: G. Bringmann, M. Breuning, unpublished results.
53. G. Bringmann, J.-P. Geisler, Tetrahedron Lett. 1989, 30, 317-320.
54. [10] the stereodescriptor at the biaryl axis changes from M to P.
55. G. M. Sheldrick, Program Package SHELXTL-PLUS, Release 4.1, Siemens Analytical Instruments Inc., Madison, WI 53719, (USA) 1990.