Diastereoselective Diels-Alder reactions of N-sulfonyl-1-aza-1,3-butadienes with optically active enol ethers: An asymmetric variant of the 1-azadiene Diels-Alder reaction

Journal of the American Chemical Society

Volumn 128, Issue 8, 2006, Pages 2587-2593

  Clark, Ryan C ^a   Pfeiffer, Steven S ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; PHASE TRANSITIONS; REACTION KINETICS;

ASYMMETRIC DIELS-ALDER REACTION; CYCLOADDITION TRANSITION STATE; ROOM-TEMPERATURE;

BUTADIENE;

1,3 BUTADIENE; ETHER DERIVATIVE; N SULFONYL 1 AZA 1,3 BUTADIENE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLOADDITION; DERIVATIZATION; DIELS ALDER REACTION; DRUG ISOLATION; PHASE TRANSITION; PURIFICATION; REACTION ANALYSIS; STEREOCHEMISTRY;

AZA COMPOUNDS; BUTADIENES; ETHERS; STEREOISOMERISM;

EID: 33644647014     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0571646     Document Type: Article

References (40)

1. (a) Boger, D. L.; Kasper, A. M. J. Am. Chem. Soc. 1989, 111, 1517.
2. (b) Boger, D. L.; Corbett, W. L.; Wiggins, J. M. J. Org. Chem. 1990, 55, 2999.
3. (c) Boger, D. L.; Curran, T. T. J. Org. Chem. 1990, 55, 5439.
4. (d) Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc. 1991, 113, 1713.
5. (e) Boger, D. L.; Corbett, W. L. J. Org. Chem. 1993, 58, 2068.
6. (a) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: San Diego, 1987.
7. (b) Boger, D. L. Tetrahedron 1983, 39, 2869.
8. (c) Boger, D. L. Chem. Rev. 1986, 86, 781.
9. (d) Boger, D. L. Chemtracts: Org. Chem. 1996, 9, 149.
10. Boger, D. L.; Cassidy, K. C.; Nakahara, S. J. Am. Chem. Soc. 1993, 115, 10733.
11. Boger, D. L.; Hüter, O.; Mbiya, K.; Zhang, M. J. Am. Chem. Soc. 1995, 117, 11839.
12. Boger, D. L.; Hong, J. J. Am. Chem. Soc. 1998, 120, 1218.
13. Boger, D. L.; Blagg, B. S. J. Tetrahedron 2002, 55, 6343.
14. Schnermann, M. J.; Boger, D. L. J. Am. Chem. Soc. 2005, 127, 15704.
15. Posner, G. H.; Wettlaufer, D. G. Tetrahedron Lett. 1986, 27, 667.
16. (a) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007.
17. (b) Dujardin, G.; Rossignol, S.; Brown, E. Synthesis 1998, 763.
18. (c) Gong, J.; Bonfand, E.; Brown, E.; Dujardin, G.; Michelet, V.; Genêt, J. Tetrahedron Lett. 2003, 44, 2141.
19. (d) Gaulon, C.; Dhal, R.; Chapin, T.; Maisonneuve, V.; Dujardin, G. J. Org. Chem. 2003, 68, 4338.
20. Gizecki, P.; Dhal, R.; Poulard, C.; Gosselin, P.; Dujardin, G. J. Org. Chem. 2004, 37, 4007.
21. Review: Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137.
22. Pettus, T. R. R.; Selenski, C. J. Org. Chem. 2004, 69, 9196.
23. Watanabe, W. H.; Conlon, L. E. J. Am. Chem. Soc. 1957, 79, 2828.
24. Tan, D. S.; Schreiber, S. L. Tetrahedron Lett. 2000, 41, 9509.
25. Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1995, 36, 1653.
26. Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124, 1590.
27. Bosch, M.; Schlaf, M. J. Org. Chem. 2003, 68, 5225.
28. Atomic coordinates for the major cycloadducts derived from the reaction of 1 with 3a (3b, CCDC286828), 6a (6b, CCDC286829), 12a (12b, CCDC286826), 17a (17b, CCDC286830), and 19a (19b, CCDC286827, (S)-enantiomer) and for the major cycloadduct from the reaction of 21a with 19a (21b, CCDC287011, (S)-enantiomer) have been deposited with the Cambridge Crystallographic Data Center.
29. Denmark, S. E.; Schnute, M. E. J. Org. Chem. 1991, 56, 6738.
30. Denmark, S. E.; Thorarensen, A. J. Org. Chem. 1996, 61, 6727.
31. Swindell, C. S.; Tao, M. J. Org. Chem. 1993, 58, 5889.
32. (a) Prapansiri, V.; Thornton, E. R. Tetrahedron Lett. 1991, 32, 3147.
33. (b) Dujardin, G.; Molato, S.; Brown, E. Tetrahedron: Asymmetry 1993, 4, 193.
34. Sarairi, D.; Maurey, G. Bull. Soc. Chim. Fr. 1987, 297.
35. Perhaps the most expedient approach to either enantiomer of 3-hydroxy-2-pyrrolidinone is Amano PS-C lipase-mediated alcoholysis of racemic 3-acetoxy-2-pyrrolidinone (>99% ee of either enantiomer at 50% conversion, er = 1057): Kamal, A.; Ramana, K. V.; Ramana, A. V.; Babu, A. H. Tetrahedron: Asymmetry 2003, 14, 2587.
36. R = 15.3 (3R) and 17.0 (3S) min, α = 1.11.
37. Juarist, E.; Cuervas, G. Tetrahedron 1992, 48, 5019.
38. Liu, J.; Niwayama, Y. Y.; You, Y.; Houk, K. N. J. Org. Chem. 1998, 63, 1064.
39. Sun, P.; Weinreb, S. M.; Shang, M. J. Org. Chem. 1997, 62, 8604.
40. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353. 2594-2603