Novel boronic acid Mannich reactions of α,α-dichloro- and α,α,ω-trichloroaldehydes with arylboronic acids

Synthesis

Volumn , Issue 3, 2007, Pages 0433-0441

  Stas, Sara ^a   Tehrani, Kourosch Abbaspour ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

Addition reactions; Boron; Mannich bases; Petasis reaction

Indexed keywords

DICHLOROMETHYLENE GROUP; MANNICH BASES; MASKED CARBONYL GROUP; PETASIS REACTION;

ADDITION REACTIONS; ALDEHYDES; BORON; KETONES; TOLUENE;

ORGANIC ACIDS;

1 (2,5 DIMETHOXYPHENYL) 1 MORPHOLINOPROPAN 2 ONE; 1 (4 CHLOROPHENYL) 1 MORPHOLINOPROPAN 2 ONE; 1 (4 ETHOXYPHENYL) 1 MORPHOLINOPROPAN 2 ONE; 1 CYCLOPROPYL 2 MORPHOLINO 2 PHENYLETHANONE; 1 MORPHOLINO 1 (4 TOLYL)PROPAN 2 ONE; 1 MORPHOLINO 1 PHENYLBUTAN 2 ONE; 1 MORPHOLINO 1 PHENYLHEPTAN 2 ONE; 1 MORPHOLINO 1 PHENYLPROPAN 2 ONE; 2 METHYL 2 MORPHOLINO 4 PHENYLBUT 3 ENAL; 2 MORPHOLINO 1 PHENYLPROPAN 2 ONE; 2,2 DICHLOROBUTANAL; 3 METHYL 1 MORPHOLINO 1 PHENYLBUTAN 2 ONE; 3 MORPHOLINO 5 PHENYLPENT 4 ENE 2 ONE; 4 METHYL 4 MORPHOLINO 1,6 DIPHENYLHEX 5 EN 3 ONE; 5 PHENYLPENTANE 2,3 DIONE; 6 CHLORO 1 MORPHOLINO 1 PHENYLHEXAN 2 ONE; ALDEHYDE; ALKANONE; BORONIC ACID DERIVATIVE; DIKETONE; KETONE; MORPHOLINE; TOLUENE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; MANNICH REACTION; ONE POT SYNTHESIS;

EID: 33947506522     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965880     Document Type: Article

References (56)

1. (a) Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583.
2. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445.
3. (c) Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 53, 16463.
4. (d) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798.
5. (e) Petasis, N. A.; Patel, Z. D. Tetrahedron Lett. 2000, 41, 9607.
6. (f) Petasis, N. A.; Boral, S. Tetrahedron Lett. 2001, 42, 539.
7. Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron 2000, 56, 10023.
8. (a) Klopfenstein, S. R.; Chen, J. J.; Golebiowski, A.; Li, M.; Peng, S. X.; Shao, X. Tetrahedron Lett. 2000, 41, 4835.
9. (b) Golebiowski, A.; Klopfenstein, S. R.; Chen, J. J.; Shao, X. Tetrahedron Lett. 2000, 41, 4841.
10. (c) Thompson, K. A.; Hall, D. G. Chem. Commun. 2000, 2379.
11. (a) Portlock, D. E.; Naskar, D.; West, L.; Ostaszewski, R.; Chen, J. J. Tetrahedron Lett. 2003, 44, 5121.
12. (b) Naskar, D.; Roy, A.; Seibel, W. L.; West, L.; Portlock, D. E. Tetrahedron Lett. 2003, 44, 6297.
13. (c) Portlock, D. E.; Ostaszewski, R.; Naskar, D.; West, L. Tetrahedron Lett. 2003, 44, 603.
14. Grigg, R.; Sridharan, V.; Thayaparan, A. Tetrahedron Lett. 2003, 44, 9017.
15. (a) Follmann, M.; Graull, F.; Schäfer, T.; Kopec, S.; Hamley, P. Synlett 2005, 1009.
16. (b) McLean, N. J.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2004, 45, 993.
17. Nanda, K. K.; Trotter, B. W. Tetrahedron Lett. 2005, 46, 2025.
18. Jiang, B.; Yang, C.-G.; Gu, X.-H. Tetrahedron Lett. 2001, 42, 2545.
19. Hansen, T. K.; Schlienger, N.; Hansen, B. S.; Andersen, P. H.; Bryce, M. R. Tetrahedron Lett. 1999, 40, 3651.
20. Naskar, D.; Roy, A.; Seibel, W. L.; West, L.; Portlock, D. E. Tetrahedron Lett. 2003, 44, 8865.
21. (a) Prakash, G. K. S.; Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. Org. Lett. 2000, 2, 3173.
22. (b) Prakash, G. K. S.; Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. J. Org. Chem. 2002, 67, 3718.
23. (a) Davis, A. S.; Pyne, S. G.; Skelton, B. W.; White, A. H. J. Org. Chem. 2004, 69, 3139.
24. (b) Au, C. W. G.; Pyne, S. G. J. Org. Chem. 2006, 71, 7097.
25. Schlienger, N.; Bryce, M. R.; Hansen, T. K. Tetrahedron Lett. 2000, 41, 1303.
26. (a) Harwood, L. M.; Currie, G. S.; Drew, M. G. B.; Luke, R. W. A. Chem. Commun. 1996, 1953.
27. (b) Currie, G. S.; Drew, M. G. B.; Harwood, L. M.; Hughes, D. J.; Luke, R. W. A.; Vickers, R. J. J. Chem. Soc., Perkin Trans. 1 2000, 2982.
28. (a) Berrée, F.; Debache, A.; Marsac, Y.; Carboni, B. Tetrahedron Lett. 2001, 42, 3591.
29. (b) Berrée, F.; Debache, A.; Marsac, Y.; Collet, B.; Girard-Le Bleiz, P.; Carboni, B. Tetrahedron 2006, 62, 4027.
30. De Kimpe, N.; Stevens, C. Tetrahedron 1991, 47, 3407.
31. Bellesia, F.; De Buyck, L.; Ghelfi, F.; Pagnoni, U. M.; Parsons, A. F.; Pinetti, A. Synthesis 2003, 2173.
32. Wang, Q.; Finn, M. G. Org. Lett. 2000, 2, 4063.
33. Mousseron, M.; Jullien, J.; Jolchine, Y. Bull. Soc. Chim. Fr. 1952, 757.
34. Stevens, C. L.; Pillai, P. M. J. Org. Chem. 1972, 37, 173.
35. Abbaspour Tehrani, K.; Stas, S. unpublished results.
36. Vedejs, E.; Chapman, R. W.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3020.
37. (a) Fisher, L. E.; Muchowski, J. M. Org. Prep. Proced. Int. 1990, 22, 399.
38. (b) O'Neill, B. T. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, 397.
39. (c) Reetz, M. T.; Drewes, M. W.; Lenick, K.; Schmitz, A.; Holdgrun, X. Tetrahedron: Asymmetry 1990, 1, 375.
40. (d) Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15.
41. (e) Singh, J.; Satyamurthi, N.; Aidhen, I. S. J. Prakt. Chem. 2000, 342, 340.
42. Massa, S.; Di Santo, R.; Mai, A.; Artico, M.; Pantaleoni, G.; Giorgi, R.; Coppolino, M. F. Arch. Pharm. (Weinheim, Ger.) 1992, 325, 403.
43. Gevorkyan, G. A.; Gabrielyan, S. A.; Apoyan, N. A.; Podol'skaya, L. P.; Sukasyan, R. S.; Sarkisyan, A. S.; Azlivyan, A. S.; Akopyan, A. V.; Mndzhoyan, O. L. Khim.-Farm. Zh. 1989, 23, 1478;
44. Chem. Abstr. 1990, 112, 172258.
45. Di Santo, R.; Costi, R.; Roux, A.; Artico, M.; Befani, O.; Meninno, T.; Agostinelli, E.; Palmegiani, P.; Turini, P.; Cirilli, R.; Ferretti, R.; Gallinella, B.; La Torre, F. J. Med. Chem. 2005, 48, 4220.
46. Adam, W.; Ahrweiler, M.; Paulini, K.; Reißig, H.-U.; Voerckel, V. Chem. Ber. 1992, 125, 2719.
47. Satoh, T.; Kaneko, Y.; Sakata, K.; Yamakawa, K. Bull. Chem. Soc. Jpn. 1986, 59, 457.
48. Katritzky, A. R.; Cheng, D.; Musgrave, R. P. Heterocycles 1996, 42, 273.
49. (a) De Buyck, L.; Menke, N.; Louagie, J. Bull. Soc. Chim. Belg. 1991, 100, 187.
50. (b) De Buyck, L.; De Lepeleire, C. Bull. Soc. Chim. Belg. 1990, 99, 553.
51. De Buyck, L.; Casaert, F.; De Lepeleire, C.; Schamp, N. Bull. Soc. Chim. Belg. 1988, 97, 525.
52. De Buyck, L.; Verhé, R.; De Kimpe, N.; Courtheyn, D.; Schamp, N. Bull. Soc. Chim. Belg. 1980, 89, 441.
53. Southwood, T. J.; Curry, M. C.; Hutton, C. A. Tetrahedron 2006, 62, 236.
54. (a) Duhamel, P.; Duhamel, L.; Truxillo, V. Tetrahedron Lett. 1974, 51.
55. (b) Conrow, R.; Portoghese, P. S. J. Org. Chem. 1986, 51, 938.
56. (c) Gopal, D.; Nadkarrni, D. V.; Sayre, L. M. Tetrahedron Lett. 1998, 39, 1877.