Asymmetric synthesis of overcrowded alkenes by transfer of axial single bond chirality to axial double bond chirality

Angewandte Chemie - International Edition

Volumn 38, Issue 18, 1999, Pages 2738-2741

  Geertsema, Edzard M ^a   Meetsma, Auke ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Alkenes; Asymmetric synthesis; Biaryls chirality; Helical structures

Indexed keywords

ALKENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY ANALYSIS;

EID: 0033578897     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990917)38:18<2738::AID-ANIE2738>3.0.CO;2-Z     Document Type: Article

References (43)

1. a) J. Sandström in Topics in Stereochemistry, Vol. 14 (Eds.: N. L. Allinger, E. L. Eliel, S. H. Wilen), Wiley, New York, 1983;
2. b) J. H. Day, Chem. Rev. 1963, 63, 65;
3. c) W. T. Grubb, G. B. Kistiakowsky, J. Am. Chem. Soc. 1950, 72, 419;
4. d) "Photochromism, Molecules and Systems" in Studies in Organic Chemistry 40 (Eds.: H. Dürr, H. Bouas Laurent), Elsevier, Amsterdam, 1990;
5. e) A. Schönberg, U. Sodtke, K. Praefcke, Tetrahedron Lett. 1968, 3253;
6. f) A. Schönberg, U. Sodtke, K. Praefcke, Chem. Ber. 1969, 102, 1453;
7. g) R. Korenstein, K. A. Muszkat, E. Fisher, Chem. Phys. Lett. 1975, 36, 509;
8. h) R. Korenstein, K. A. Muszkat, E. Fisher, Mol. Photochem. 1972, 3, 379;
9. i) R. Korenstein, K. A. Muszkat, E. Fisher, J. Photochem. 1976, 5, 447;
10. j) R. Korenstein, K. A. Muszkat, E. Fisher, Helv. Chim. Acta 1970, 53, 2102;
11. k) Y. Tapuhi, O. Kalisky, I. Agranat, J. Org. Chem. 1979, 44, 1949;
12. l) I. Agranat, Y. Tapuhi, J. Y. Lallemand, Nouv. J. Chim. 1979, 3, 59;
13. m) I. Agranat, Y. Tapuhi, Nouv. J. Chim. 1977, 1, 361;
14. n) I. Agranat, Y. Tapuhi, J. Am. Chem. Soc. 1978, 100, 5604;
15. o) I. Agranat, Y. Tapuhi, J. Am. Chem. Soc. 1979, 101, 665;
16. p) G. Kortüm, Ber. Bunsen-Ges. Phys. Chem. 1974, 78, 391.
17. For reviews on molecular switches, see a) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267;
18. b) B. L. Feringa, N. P. M. Huck, A. M. Schoevaars, Adv. Mater. 1996, 8, 681;
19. c) W. F. Jager, J. C. de Jong, B. de Lange, N. P. M. Huck, A. Meetsma, B. L. Feringa, Angew. Chem. 1995, 107, 346; Angew. Chem. Int. Ed. Engl. 1995, 34, 348.
20. c) W. F. Jager, J. C. de Jong, B. de Lange, N. P. M. Huck, A. Meetsma, B. L. Feringa, Angew. Chem. 1995, 107, 346; Angew. Chem. Int. Ed. Engl. 1995, 34, 348.
21. a) B. L. Feringa, N. P. M. Huck, H. A. van Doren, J. Am. Chem. Soc. 1995, 117, 9929;
22. b) N. P. M. Huck, W. F. Jager, B. de Lange, B. L. Feringa, Science 1996, 273, 1686.
23. M. L. C. M. Oosterling, A. M. Schoevaars, H. J. Haitjema, B. L. Feringa, lsr. J. Chem. 1996, 36, 341.
24. W. F. Jager, B. de Lange, A. M. Schoevaars, F. van Bolhuis, B. L. Feringa, Tetrahedron: Asymmetry 1993, 4, 1481.
25. a) S. Miyano, H. Fukushima, S. Handa, H. Ito, H. Hashimoto, Bull. Chem. Soc. Jpn. 1988, 61, 3249, and references therein;
26. b) B. H. Lipshutz, Z. Liu, F. Kayser, Tetrahedron Lett. 1994, 35, 5567;
27. c) M. Tanaka, H. Mitsuhashi, M. Maruno, T. Wakamatsu, Tetrahedron Lett. 1994, 35, 3733;
28. d) V. H. Rawal, A. S. Florjancic, S. P. Singh, Tetrahedron Lett. 1994, 35, 8985;
29. e) K. S. Feldman, A. Sambandam, J. Org. Chem. 1995, 60, 8171;
30. f) T. Sugimura, H. Yamada, S. Inoue, A. Tai, Tetrahedron: Asymmetry 1997, 8, 649.
31. a) Y. C. Yip, X. Wang, D. K. P. Ng, T. C. W. Mak, P. Chiang, T. Luh, J. Org. Chem. 1990, 55, 1881.
32. b) X. Wang, T. Luh, J. Org. Chem. 1989, 54, 263.
33. Compound 3 was prepared from 4-methoxybenzenethiol and 4-bromoisophthalic acid in a two-step procedure.
34. a) A. Schönberg, S. Nickel, Chem. Ber. 1934, 67, 1795;
35. b) A. Schönberg, W. Asker, J. Chem. Soc. 1942, 272;
36. c) A. Schönberg, A. Mustafa, M. E. El-Din Sobhy, J. Am. Chem. Soc. 1953, 75, 3377;
37. d) A. Mustafa, M. E. El-Din Sobhy, J. Am. Chem. Soc. 1955, 77, 5124;
38. e) A. Mustafa, W. Asker, M. E. El-Din Sobhy, J. Org. Chem. 1960, 25, 1519.
39. The chirality of this type of helical-shaped distorted alkenes is described by the helicity rule, with P (plus) for a right-handed helix and M (minus) for a left-handed helix, see for example, R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413: Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
40. The chirality of this type of helical-shaped distorted alkenes is described by the helicity rule, with P (plus) for a right-handed helix and M (minus) for a left-handed helix, see for example, R. S. Cahn, C. K. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413: Angew. Chem. Int. Ed. Engl. 1966, 5, 385.
41. The model of (R,M)-7 was constructed by using Quanta97/CHARMm, which is a product of Molecular Simulations Inc., San Diego, USA. Internet: http://www.msi.com. Dr. Franck Schoonbeek is acknowledged for his assistance.
42. K. Nozaki, T. Terakawa, H. Takaya, T. Hiyama, Angew. Chem. 1998, 110, 138; Angew. Chem. Int. Ed. 1998, 37, 131.
43. K. Nozaki, T. Terakawa, H. Takaya, T. Hiyama, Angew. Chem. 1998, 110, 138; Angew. Chem. Int. Ed. 1998, 37, 131.