Diastereoselective reaction of 1-(arylsulfinyl)-2-naphthaldehydes

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4157-4160

  Nakamura, Shuichi ^a   Yasuda, Hiroki ^a   Watanabe, Yoshihiko ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric reaction; Atropisomerism; Grignard reactions; Sulfoxides

Indexed keywords

ALDEHYDE DERIVATIVE; METHANOL DERIVATIVE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; MOLECULAR MODEL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034729175     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00557-8     Document Type: Article

References (40)

1. (a) Curran, D. P.; Qi, H.; Geib, S. J.; Demello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
2. (b) Kishikawa, K.; Tsuru, I.; Kohmoto, S.; Yamamoto, M.; Yamada, K. Chem. Lett. 1994, 1605.
3. (c) Curran, D. P.; Geib, S.; DeMello, N. Tetrahedron 1999, 55, 5681.
4. (a) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
5. (b) Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447.
6. (c) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634.
7. (d) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967.
8. (e) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295.
9. (f) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949.
10. (g) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett. 1999, 40, 8827.
11. (h) Bach, T.; Schröder, J.; Harms, K. Tetrahedron Lett. 1999, 40, 9003.
12. (i) Curran, D. P.; Liu, W.; Chen, C. H. J. Am. Chem. Soc. 1999, 121, 11012.
13. (a) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1996, 37, 5577.
14. (b) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3329.
15. (c) Clayden, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 949.
16. (d) Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8323.
17. (e) Bragg, R. A.; Clayden, J. Tetrahedron Lett. 1999, 40, 8327.
18. (f) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 7883.
19. (a) Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899.
20. (b) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556.
21. (a) Casarini, D.; Foresti, E.; Gasparrini, F.; Lunazzi, L.; Macciantelli, D.; Misiti, D.; Villani, C. J. Org. Chem. 1993, 58, 5674.
22. (b) Casarini, D.; Lunazzi, L.; Gasparrini, F.; Villani, C.; Cirilli, M.; Gavuzzo, E. J. Org. Chem. 1995, 50, 97.
23. (c) Jennings, W. B.; Kochanewycz, M. J.; Lunazzi, L. J. Chem. Soc., Perkin Trans. 2 1997, 2271.
24. (d) Baker, R. W.; Kyasnoor, R. V.; Sargent, M. V. J. Chem. Soc., Perkin Trans. 2 1998, 1333.
25. Lett, R.; Marquet, A. Tetrahedron Lett. 1974, 30, 3379.
26. (a) Oki, M. In Applications of Dynamic NMR Spectroscopy to Organic Chemistry; VCH: Deerfield Beach, FL, 1985, 160.
27. (b) Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W.; McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron 1998, 54, 13 277.
28. In contrast with our results, Clayden et al. have reported the reversal in stereoselectivity in each reaction of 2-formyl-1-naphthamides with RMgX or RLi, which can be ascribed to a chelated (RMgX) or non-chelated (RLi) transition state, see: Ref. 3a.
29. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392.
30. The MO calculation by the MOPAC93/PM3 method showed a similar optimized structure for 1d, the energy difference of which from the less stable conformer was 1.81 kcal/mol.
31. 2. These results will be reported in due course.
32. Prepared from the reaction of 1-lithio-2-dimethoxymethylnaphthalene and the DAG-sulfinate and subsequent hydrolysis. For the preparation of the DAG-sulfinate, see: (a) Mase, N.; Watanabe, Y.; Ueno, Y.; Toru, T. J. Org. Chem. 1997, 62, 7794.
33. (b) Watanabe, Y.; Mase, N.; Tateyama, M.; Toru, T. Tetrahedron: Asymmetry 1999, 10, 737.
34. (a) Lockard, J. P.; Schroeck, C. W.; Johnson, C. R. Synthesis 1973, 485.
35. (b) Durst, T.; LeBelle, M. J.; Elzen, R. V.; Tin, K.-C. Can. J. Chem. 1974, 52, 761.
36. (c) Sato, T.; Kaneko, Y.; Yamakawa, K. Tetrahedron Lett. 1986, 27, 2379.
37. (d) Furukawa, N.; Ogawa, S.; Matsumura, K.; Fujihara, H. J. Org. Chem. 1991, 56, 6341.
38. The optical purity was confirmed by the HPLC analysis (Chiralcel OD-H).
39. (a) Seebach, D.; Beck, A. K.; Roggo, S.; Wonnacott, A. Chem. Ber. 1985, 118, 3673.
40. (b) Soai, K.; Kawase, Y.; Oshio, A. J. Chem. Soc. Perkin Trans. 1 1991, 1613.