Synthesis and applications of (1R,5S,6S)-6-(2,2-dimethylpropanamido)spiro[4.4]nonan-1-ol as a chiral auxiliary in Diels-Alder reactions

Tetrahedron Asymmetry

Volumn 11, Issue 13, 2000, Pages 2733-2739

  Burke, Michael J ^a   Allan, Murray M ^a   Parvez, Masood ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6 (2,2 DIMETHYLPROPANAMIDO)SPIRO[4.4]NONAN 1 OL; AMINOALCOHOL; BROMOBENZOIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034647803     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00242-1     Document Type: Article

References (40)

1. (a) Nieman, J. A.; Keay, B. A. Tetrahedron: Asymmetry 1996, 7, 3521.
2. (b) Nieman, J. A.; Keay, B. A. Synth. Commun. 1999, 29, 3829.
3. (c) Nieman, J. A.; Keay, B. A.; Kubicki, M.; Yang, D.; Rauk, A.; Tsankov, D.; Wieser, H. J. Org. Chem. 1995, 60, 1918.
4. (d) Nieman, J. A.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1993, 4, 1973.
5. (e) Nieman, J. A.; Keay, B. A. Tetrahedron: Asymmetry 1995, 6, 1575.
6. (f) Keay, B. A.; Maddaford, S. P.; Cristofoli, W. A.; Andersen, N. G.; Passafaro, M. S.; Wilson, N. S.; Nieman, J. A. Can. J. Chem. 1997, 75, 1163.
7. For other uses of spiro[4.4]nonane-1,6-diol as a chiral auxiliary, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570. (b) Hu, W.; Yan, M.; Lau, C-P.; Yang, S. M.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 973. (c) Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croatica Chem. Acta 1996, 69, 459. (d) Srivastava, N.; Mital, A.; Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493.
8. For other uses of spiro[4.4]nonane-1,6-diol as a chiral auxiliary, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570. (b) Hu, W.; Yan, M.; Lau, C-P.; Yang, S. M.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 973. (c) Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croatica Chem. Acta 1996, 69, 459. (d) Srivastava, N.; Mital, A.; Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493.
9. For other uses of spiro[4.4]nonane-1,6-diol as a chiral auxiliary, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570. (b) Hu, W.; Yan, M.; Lau, C-P.; Yang, S. M.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 973. (c) Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croatica Chem. Acta 1996, 69, 459. (d) Srivastava, N.; Mital, A.; Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493.
10. For other uses of spiro[4.4]nonane-1,6-diol as a chiral auxiliary, see: (a) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570. (b) Hu, W.; Yan, M.; Lau, C-P.; Yang, S. M.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 973. (c) Seebach, D.; Beck, A. K.; Dahinden, R.; Hoffmann, M.; Kühnle, F. N. M. Croatica Chem. Acta 1996, 69, 459. (d) Srivastava, N.; Mital, A.; Kumar, A. J. Chem. Soc., Chem. Commun. 1992, 493.
11. For some recent reports on the use of other spiro systems, see: (a) Arai, M. A.; Arai, T.; Sasai, H. Org. Lett. 1999, 1, 1795. (b) Sirbu, D.; Falck-Pedersen, M. L.; Rømming, C.; Undheim, K. Tetrahedron 1999, 55, 6703. (c) Birman, V. B.; Rheingold, A. L.; Lam, K.-C. Tetrahedron: Asymmetry 1999, 10, 125.
12. For some recent reports on the use of other spiro systems, see: (a) Arai, M. A.; Arai, T.; Sasai, H. Org. Lett. 1999, 1, 1795. (b) Sirbu, D.; Falck-Pedersen, M. L.; Rømming, C.; Undheim, K. Tetrahedron 1999, 55, 6703. (c) Birman, V. B.; Rheingold, A. L.; Lam, K.-C. Tetrahedron: Asymmetry 1999, 10, 125.
13. For some recent reports on the use of other spiro systems, see: (a) Arai, M. A.; Arai, T.; Sasai, H. Org. Lett. 1999, 1, 1795. (b) Sirbu, D.; Falck-Pedersen, M. L.; Rømming, C.; Undheim, K. Tetrahedron 1999, 55, 6703. (c) Birman, V. B.; Rheingold, A. L.; Lam, K.-C. Tetrahedron: Asymmetry 1999, 10, 125.
14. For examples in which other spiro systems have been used as chiral auxiliaries, see: (a) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Grant, K. J.; Hodgson, P. K. G.; Thorburn, P. Heterocycles 1994, 37, 199. (b) Dinesh, C. U.; Kumar, P.; Reddy, R. S.; Pandey, B.; Puranik, V. G. Tetrahedron: Asymmetry 1995, 6, 2961.
15. For examples in which other spiro systems have been used as chiral auxiliaries, see: (a) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Grant, K. J.; Hodgson, P. K. G.; Thorburn, P. Heterocycles 1994, 37, 199. (b) Dinesh, C. U.; Kumar, P.; Reddy, R. S.; Pandey, B.; Puranik, V. G. Tetrahedron: Asymmetry 1995, 6, 2961.
16. Mathivanan, P.; Maitra, U. J. Org. Chem. 1995, 60, 364.
17. (a) Denmark, S. E.; Borow, R. L. J. Org. Chem. 1990, 55, 5926.
18. (b) Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742.
19. (c) Ahn, K. H.; Lim, A.; Lee, S. Tetrahedron: Asymmetry 1993, 4, 2435.
20. (d) Ahn, K. H.; Lee, S.; Lim, A. J. Org. Chem. 1992, 57, 5065.
21. (e) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 56, 3211 and 4913.
22. (f) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995.
23. (a) Vavon, H. Bull. Soc. Chim. Fr. 1934, 1703.
24. (b) Christol, H.; Mousseron, M.; Plenat, F. Bull. Soc. Chim. Fr. 1959, 543.
25. (c) Bien, S.; Ovadia, D. J. Org. Chem. 1974, 39, 2258.
26. (d) Fraga, C.; Barreiro, E. J. Synth. Commun. 1995, 25, 1133
27. Trost, B.; Radinov, R.; Grenzer, E. J. Am. Chem. Soc. 1997, 119, 7879.
28. The allylation of 10 with a variety of chiral phosphine catalysts never gave a % ee greater than 15%.
29. (a) Allan, M. M.; Ramsden, P. D.; Burke, M. J.; Parvez, M.; Keay, B. A. Tetrahedron: Asymmetry 1999, 10, 3099.
30. (b) Fraga, C. A. M.; Barreiro, E. J. Chirality 1996, 8, 305.
31. (c) Fraga, C. A. M.; Barreiro, E. J.; Silva, E. F.; Santos, A. R.; Ramos, M. C. K. V.; Aquino Neto, F. R. Chirality 1997, 9, 321.
32. Compound (-)-(2R)-10 can also be used to synthesize the antipode (-)-7. Reduction of (-)-(2R)-10 with t-butyldiisobutylaluminium hydride provides (-)-(1S,2R)-12.
33. Zwierzak, A. Phosphorus, Sulfur Silicon and the Related Elements 1993, 75, 51.
34. Prempree, P.; Siwapinyoyos, T.; Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron Lett. 1980, 21, 1169.
35. w = 0.157 and the Flack parameter = 1.01(2) and was therefore rejected as the absolute configuration present in the crystal.
36. Interestingly, the initial product from the reaction of (+)-7 with trans-crotonyl chloride was ester 28 with a unconjugated double bond. Treatment of ester 28 with cat. p-TsOH in THF at reflux for 24 h provided (-)-21 in quantitative yield. (Matrix Presented)
37. 3): Oppolzer, W.; Wills, M.; Kelly, M. J.; Signer, M.; Blagg, J. Tetrahedron Lett. 1990, 31, 5015.
38. D +34.8 (EtOH): Cervinko, O.; Kriz, O. Collect. Czech. Chem. Commun. 1968, 33, 2342.
39. D +107 (c 4.07, 95% EtOH): Argenti, L.; Bellina, F.; Carpita, A.; Rossi, R. Synth. Commun. 1995, 25, 2909.
40. 3): Kouklovsky, C.; Pouihès, A.; Langlois, Y. J. Am. Chem. Soc. 1990, 112, 6672.