Asymmetric synthesis of 2-substituted hexahydroquinolin-4-ones using a Pd-catalyzed asymmetric allylic amination and intramolecular Mannich reaction: Catalytic asymmetric synthesis of 2-epi-cis-195A

Synthesis

Volumn , Issue 16, 2011, Pages 2540-2548

  Kakugawa, Kazumi ^a   Nemoto, Tetsuhiro ^a   Kohno, Yuta ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

asymmetric allylic amination; asymmetric synthesis; chiral diaminophosphine oxide; decahydroquinoline alkaloid; intramolecular Mannich reaction; palladium

Indexed keywords

ALLYLIC AMINATION; ASYMMETRIC SYNTHESIS; CHIRAL DIAMINOPHOSPHINE OXIDE; DECAHYDROQUINOLINE ALKALOID; MANNICH REACTIONS;

AMINES; CATALYSIS;

SYNTHESIS (CHEMICAL);

1 (4 METHOXYBENZYL) 2 PROPYL 2,3,6,7,8,8A HEXAHYDRO 1H QUINOLIN 4 ONE; 1 (4 METHOXYBENZYL) 5 METHYL 2 PROPYLOCTAHYDROQUINOLIN 4 ONE; 195A; 2 EPI 195A; 2 SUBSTITUTED HEXAHYDROQUINOLINE 4 ONE DERIVATIVE; 223F; 4 HYDROXY 1 (4 METHOXYBENZYL) 2 PROPYL 1,2,6,7,8,8A HEXAHYDROQUINOLINE 3 CARBOXYLIC ACID ALLYL ESTER; ALKALOID DERIVATIVE; DECAHYDROQUINOLINE DERIVATIVE; GEPHYROTOXIN; PALLADIUM; PUMILIOTOXIN C; TRIFLUOROMETHANESULFONIC ACID 1 (4 METHOXYBENZYL) 5 METHYL 2 PROPYL 1,2,3,5,6,7,8,8A OCTAHYDROQUINOLIN 4 YL ESTER; TRIFLUOROMETHANESULFONIC ACID 1 (4 METHOXYBENZYL) 5 METHYL 2 PROPYL 1,2,4A,5,6,7,8,8A OCTAHYDROQUINOLIN 4 YL ESTER; UNCLASSIFIED DRUG;

ALLYLIC AMINATION; AMINATION; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; MANNICH REACTION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; PROCESS DEVELOPMENT; RACEMIC MIXTURE;

EID: 80051547367     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260102     Document Type: Article

References (75)

1. Daly J W., Tokuyama T, Habermehl G, Karle I L., Witkop B, Liebigs Ann. Chem. 1969 729 198
2. Tokuyama T, Nishimori N, Karle I L., Edwards M W., Daly J W., Tetrahedron 1986 42 3453
3. Tokuyama T, Tsujita T, Shimada A, Garraffo H M., Spande T F., Daly J W., Tetrahedron 1991 47 5401
4. Garraffo H M., Caceres J, Daly J W., Spande T F., Andriamaharavo N R., Andriantsiferana M, J. Nat. Prod. 1993 56 1016
5. Daly J W., Ware N, Saporito R A., Spande T F., Garraffo H M., J. Nat. Prod. 2009 72 1110
6. Garraffo H M., Spande T F., Daly J W., Baldessari A, Gros E G., J. Nat. Prod. 1993 56 357
7. Steffan B, Tetrahedron 1991 47 8729
8. Davis R A., Carroll A R., Quinn R J., J. Nat. Prod. 2002 65 454
9. Wright A D., Goclik E, König G M., Kaminsky R, [nl]J. Med. Chem. 2002 45 3067
10. Kubanek J, Williams D E., DilipdeSilva E, Allen T, Andersen R J., Tetrahedron Lett. 1995 36 6189
11. Jones T H., Gorman J S. T., Snelling R R., Delabie J H. C., Blum M S., Garraffo H, Jain P, Daly J W., Spande T F., Chem. Ecol. 1999 25 1179
12. Daly J W., Garraffo H M., Jain P, Spande T F., Snelling R R., Jaramillo C, Rand A S., J. Chem. Ecol. 2000 26 73
13. Spande T F., Jain P, Garraffo H M., Pannell L K., Yeh H J. C., Daly J W., Fukumoto S, Imamura K, Tokuyama T, Torres J A., Snelling R R., Jones T H., [nl]J. Nat. Prod. 1999 62 5
14. Daly J W., Spande T F., Garraffo H M., J. Nat. Prod. 2005 68 1556
15. Daly J W., Nishizawa Y, Edwards M W., Waters J A., Aronstam R S., Neurochem. Res. 1991 16 489
16. Daly J W., Nishizawa Y, Padgett W L., Tokuyama T, McCloskey P J., Waykole L, Aronstam R S., Neurochem. Res. 1991 16 1207
17. Warnick J E., Jessup P J., Overman L E., Eldefrawi M E., Nimit Y, Daly J W., Albuquerque E X., Mol. Pharmacol. 1982 22 565
18. Akashi M, Sato Y, Mori M, J. Org. Chem. 2001 66 7873; and references cited therein
19. Girard N, Hurvois J.-P, Moinet C, Toupet L, Eur. J. Org. Chem. 2005 2269
20. Saeki M, Toyota M, Tetrahedron Lett. 2010 51 4620
21. Oppolzer W, Flaskamp E, Bieber L W., Helv. Chim. Acta 2001 84 141; and references cited therein
22. Amat M, Griera R, Fabregat R, Molins E, Bosch J, Angew. Chem. Int. Ed. 2008 47 3348
23. Lauzon S, Tremblay F, Gagnon D, Godbout C, Chabot C, Mercier-Shanks C, Perreault S, DeSeve H, Spino C, J. Org. Chem. 2008 73 6239
24. Amat M, Fabregat R, Griera R, Florindo P, Molins E, Bosch J, J. Org. Chem. 2010 75 3797
25. Dijk E W., Panella L, Pinho P, Naasz R, Meetsma A, Minnaard A J., Feringa B L., Tetrahedron 2004 60 9687
26. Neidhöfer J, Blechert S, Synthesis 2004 3047
27. Holub N, Neidhöfer J, Blechert S, Org. Lett. 2005 7 1227
28. Weymann M, Schultz-Kukula M, Kunz H, Tetrahedron Lett. 1998 39 7835
29. Fearnley S P., Thongsornkleeb C, J. Org. Chem. 2010 75 933
30. Comins D L., Dehghani A, J. Org. Chem. 1995 60 794
31. Fujimoto R, Kishi Y, Tetrahedron Lett. 1981 22 4197
32. Fujimoto R, Kishi Y, Blount J F., [nl]J. Am. Chem. Soc. 1980 102 7154
33. Wei L.-L, Hsung R P., Sklenicka H M., Gerasyuto A I., Angew. Chem. Int. Ed. 2001 40 1516
34. Santarem M, Vanucci-Bacqué C, Lhommet G, J. Org. Chem. 2008 73 6466
35. For other representative asymmetric syntheses of natural products with a bicyclic decahydroquinoline skeleton; Lepadins
36. Toyooka N, Okumura M, Takahata H, [nl]J. Org. Chem. 1999 64 2182
37. Ozawa T, Aoyagi S, Kibayashi C, Org. Lett. 2000 2 2955
38. Pu X, Ma D, Angew. Chem. Int. Ed. 2004 43 4222
39. Niethe A, Fischer D, Blechert S, J. Org. Chem. 2008 73 3088
40. Li G, Hsung R P., Slafer B W., Sagamanova I K., Org. Lett. 2008 10 4991
41. Barbe G, Charette A B., [nl] J. Am. Chem. Soc. 2008 130 13873
42. Comins D L., Brooks C A., Al-awar R S., Goehring R R., Org. Lett. 1999 1 229
43. Comins D L., Libby A H., Al-awar R S., Foti C J., J. Org. Chem. 1999 64 2184
44. Wolfe B H., Libby A H., Al-awar R S., Foti C J., Comins D L., J. Org. Chem. 2010 75 8564
45. Tanaka T, Kogure N, Kitajima M, Takayama H, J. Org. Chem. 2009 74 8675
46. Nakamura Y, Burke A M., Kotani S, Ziller J W., Rychnovsky S D., Org. Lett. 2010 12 72
47. For recent representative references for the stereoselective synthesis of functionalized decahydroquinolines, see:, Comins D L., Ollinger C G., Tetrahedron Lett. 2001 42 4115
48. Toyooka N, Okumura M, Nemoto H, [nl]J. Org. Chem. 2002 67 6078
49. Galbo F L., Occhiato E G., Guarna A, Faggi C, J. Org. Chem. 2003 68 6360
50. Gravier-Pelletier C, Maton W, Bertho G, Merrer Y L., Tetrahedron 2003 59 8721
51. Banner E J., Stevens E D., Trudell M L., Tetrahedron Lett. 2004 45 4411
52. Mena M, Bonjoch J, Tetrahedron 2005 61 8264
53. Comins D L., Kuethe J T., Miller T M., Février F C., Brooks C A., J. Org. Chem. 2005 70 5221
54. Mena M, Bonjoch J, GomezPardo D, Cossy J, J. Org. Chem. 2006 71 5930
55. Diaba F, Ricou E, Bonjoch J, Org. Lett. 2007 9 2633
56. Rueping M, Antonchick A P., Angew. Chem. Int. Ed. 2008 47 5836
57. Huang J, Bergmeier S C., Tetrahedron 2008 64 6434
58. Amat M, Fabregat R, Griera R, Bosch J, J. Org. Chem. 2009 74 1794
59. Guthmann H, Conole D, Wright E, Körber K, Barker D, Brimble M A., Eur. J. Org. Chem. 2009 1944
60. Heitbaum M, Fröhlich R, Glorius F, Adv. Synth. Catal. 2010 352 357
61. Sethofer S G., Mayer T, Toste F D., J. Am. Chem. Soc. 2010 132 8276
62. Nemoto T, Matsumoto T, Masuda T, Hitomi T, Hatano K, Hamada Y, J. Am. Chem. Soc. 2004 126 3690
63. For reviews on DIAPHOX preligands in asymmetric transition-metal catalysis, see:, Nemoto T, Chem. Pharm. Bull. 2008 56 1213
64. Nemoto T, Hamada Y, Tetrahedron 2011 67 667
65. Nemoto T, Masuda T, Akimoto Y, Fukuyama T, Hamada Y, Org. Lett. 2005 7 4447
66. Nemoto T, Fukuyama T, Yamamoto E, Tamura S, Fukuda T, Matsumoto T, Akimoto Y, Hamada Y, Org. Lett. 2007 9 927
67. Nemoto T, Tamura S, Sakamoto T, Hamada Y, Tetrahedron: Asymmetry 2008 19 1751
68. Nemoto T, Yamamoto E, Franzén R, Fukuyama T, Wu R, Fukamachi T, Kobayashi H, Hamada Y, Org. Lett. 2010 12 872
69. The M06-2X functional has been found to be reliable for weak dispersion interactions such as hydrogen-bonding interaction. The molecular energy calculation using B3LYP/6-31G** indicated that 4b is 2.12 kcal/mol more stable than 4a. For the related references, see:, Zhao Y, Truhlar D G., Acc. Chem. Res. 2008 41 157
70. Um J M., Gutierrez O, Schoenebeck F, Houk K N., MacMillan D W. C., [nl]J. Am. Chem. Soc. 2010 132 6001
71. See Supporting Information for details.
72. The enantiomeric excess was determined by chiral HPLC analysis.
73. Comins D L., Dehghani A, Foti C J., Joseph S P., Org. Synth. 1997 74 77
74. Hoffmann R W., Chem. Rev. 1989 89 1841
75. Graff M, AlDilaimi A, Seguineau P, Rambaud M, Villieras J, Tetrahedron Lett. 1986 27 1577