Ir-catalyzed asymmetric allylic alkylation using chiral diaminophosphine oxides: DIAPHOXs. Formal enantioselective synthesis of (-)-paroxetine

Tetrahedron Letters

Volumn 48, Issue 29, 2007, Pages 4977-4981

  Nemoto, Tetsuhiro ^a   Sakamoto, Tatsurou ^a   Fukuyama, Takashi ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Asymmetric allylic alkylation; Asymmetric catalysis; Diaminophosphine oxide; Iridium; Paroxetine

Indexed keywords

ACETAMIDE DERIVATIVE; DIAMINOPHOSPHINE OXIDE; IRIDIUM; N,O BIS(TRIMETHYLSILYL)ACETAMIDE; PAROXETINE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS;

EID: 34250338963     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.120     Document Type: Article

References (71)

1. For reviews on transition-metal catalyzed asymmetric allylic substitution reactions, see:. Trost B.M., and Van Vranken D.L. Chem. Rev. 96 (1996) 395-422
2. Trost B.M., and Crawley M.L. Chem. Rev. 103 (2003) 2921-2943
3. For representative examples, see:. Hayashi T., Kawatsura M., and Uozumi Y. J. Chem. Soc., Chem. Commun. (1997) 561-562
4. Prétôt R., and Pfaltz A. Angew. Chem., Int. Ed. 37 (1998) 323-325
5. You S.-L., Zhu X.-Z., Luo Y.-M., Hou X.-L., and Dai L.-X. J. Am. Chem. Soc. 123 (2001) 7471-7472
6. Pàmies O., Diéguez M., and Claver C. J. Am. Chem. Soc. 127 (2005) 3646-3647
7. Zheng W.H., Sun N., and Hou X.L. Org. Lett. 7 (2005) 5151-5154
8. Lloyd-Jones G.C., and Pfaltz A. Angew. Chem., Int. Ed. Engl. 34 (1995) 462-464
9. Trost B.M., and Hachiya I. J. Am. Chem. Soc. 120 (1998) 1104-1105
10. Trost B.M., Hildbrand S., and Dogra K. J. Am. Chem. Soc. 121 (1999) 10416-10417
11. Trost B.M., and Dogra K. J. Am. Chem. Soc. 124 (2002) 7256-7257
12. Trost B.M., Dogra K., and Franzini M. J. Am. Chem. Soc. 126 (2004) 1944-1945
13. Janssen J.P., and Helmchen G. Tetrahedron Lett. 38 (1997) 8025-8026
14. Bartels A., and Helmchen G. Chem. Commun. (1999) 741-742
15. Fuji K., Kinoshita N., Tanaka K., and Kawabata T. Chem. Commun. (1999) 2289-2290
16. Kanayama T., Yoshida K., Miyabe H., and Takemoto Y. Angew. Chem., Int. Ed. 42 (2003) 2054-2056
17. Kanayama T., Yoshida K., Miyabe H., Kimachi T., and Takemoto Y. J. Org. Chem. 68 (2003) 6197-6201
18. Kinoshita N., Marx K.H., Tanaka K., Tsubaki K., Kawabata T., Yoshikai N., Nakamura E., and Fuji K. J. Org. Chem. 69 (2004) 7960-7964
19. Alexakis A., and Polet D. Org. Lett. 6 (2004) 3529-3532
20. Lipowsky G., Miller N., and Helmchen G. Angew. Chem., Int. Ed. 43 (2004) 4595-4597
21. Streiff S., Welter C., Schelwiss M., Lipowsky G., Miller N., and Helmchen G. Chem. Commun. (2005) 2957-2959
22. Graening T., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 17192-17193
23. Polet D., Alexakis A., Tissot-Croset K., Corminboeuf C., and Ditrich K. Chem. Eur. J. 12 (2006) 3596-3609
24. Hayashi T., Okada A., Suzuka T., and Kawatsura M. Org. Lett. 5 (2003) 1713-1715
25. For enantiospecific allylic alkylation using transition metal catalysts, see Ru catalyst:. Trost B.M., Fraisse P.L., and Ball Z.T. Angew. Chem., Int. Ed. 41 (2002) 1059-1061
26. Rh catalyst:. Evans P.A., and Nelson J.D. J. Am. Chem. Soc. 120 (1998) 5581-5582
27. Evans P.A., and Leahy D.K. J. Am. Chem. Soc. 125 (2003) 8974-8975
28. Evans P.A., and Lawler M.J. J. Am. Chem. Soc. 126 (2004) 8642-8643
29. Nemoto T., Matsumoto T., Masuda T., Hitomi T., Hatano K., and Hamada Y. J. Am. Chem. Soc. 126 (2004) 3690-3691
30. Nemoto T., Masuda T., Matsumoto T., and Hamada Y. J. Org. Chem. 70 (2005) 7172-7178
31. Nemoto T., Fukuda T., Matsumoto T., Hitomi T., and Hamada Y. Adv. Synth. Catal. 347 (2005) 1504-1506
32. Nemoto T., Masuda T., Akimoto Y., Fukuyama T., and Hamada Y. Org. Lett. 7 (2005) 4447-4450
33. Nemoto T., Jin L., Nakamura H., and Hamada Y. Tetrahedron Lett. 47 (2006) 6577-6581
34. Nemoto T., Fukuyama T., Yamamoto E., Tamura S., Fukuda T., Matsumoto T., Akimoto Y., and Hamada Y. Org. Lett. 9 (2007) 927-930
35. For reviews on transition metal catalysis using phosphine oxide preligands, see:. Dubrovina N.V., and Börner A. Angew. Chem., Int. Ed. 43 (2004) 5883-5886
36. Ackermann L. Synthesis (2006) 1557-1571
37. Ackermann L. Synlett (2007) 507-526
38. Nemoto T., Sakamoto T., Matsumoto T., and Hamada Y. Tetrahedron Lett. 47 (2006) 8737-8740
39. Takeuchi R., and Kashio M. Angew. Chem., Int. Ed. 36 (1997) 263-265
40. Takeuchi R., and Kashio M. J. Am. Chem. Soc. 120 (1998) 8647-8655
41. Takeuchi R., Ue N., Tanabe K., Yamashita K., and Shiga N. J. Am. Chem. Soc. 123 (2001) 9525-9534
42. Takeuchi R. Synlett (2002) 1954-1965
43. For other representative examples of Ir-catalyzed asymmetric allylic substitution using nitrogen or oxygen nucleophiles, see:. Ohmura T., and Hartwig J.F. J. Am. Chem. Soc. 124 (2002) 15164-15165
44. Kiener C.A., Shu C., Incarvito C., and Hartwig J.F. J. Am. Chem. Soc. 125 (2003) 14272-14273
45. Shu C., and Hartwig J.F. Angew. Chem., Int. Ed. 43 (2004) 4794-4797
46. Shu C., Leiner A., and Hartwig J.F. Angew. Chem., Int. Ed. 43 (2004) 4797-4800
47. Tissot-Croset K., Polet D., and Alexakis A. Angew. Chem., Int. Ed. 43 (2004) 2426-2428
48. Lipowsky G., and Helmchen G. Chem. Commun. (2004) 896-897
49. Miyabe H., Matsumura A., Moriyama K., and Takemoto Y. Org. Lett. 6 (2004) 4631-4634
50. Leitner A., Shekhar S., Pouy M.J., and Hartwig J.F. J. Am. Chem. Soc. 127 (2005) 15506-15514
51. Weihofen R., Tverskoy O., and Helmchen G. Angew. Chem., Int. Ed. 45 (2006) 5546-5549
52. Lyothier I., Defieber C., and Carreira E.M. Angew. Chem., Int. Ed. 45 (2006) 6204-6207
53. Kimura M., and Uozumi Y. J. Org. Chem. 72 (2007) 707-714
54. For a review, see:. Helmchen G., Dahnz A., Dübon P., Schelwies M., and Weihofen R. Chem. Commun. (2007) 675-691
55. 6: 24 h, 42%, 3a/3a′ = 97/3, 45% ee. These results indicate that the counter cation of hexafluorophosphate salt might also play an important role in the present asymmetric catalysis.
56. 2, hexane/ethyl acetate: 20/1) to give (S)-3a as colorless oil (47.5 mg, 93%, 90% ee, 3a/3a′ = 99/1).
57. For a review, see:. Gunasekara N.G., Noble S., and Benfield P. Drugs 55 (1998) 85-120
58. Senda T., Ogasawara M., and Hayashi T. J. Org. Chem. 66 (2001) 6852-6856
59. Taylor M.S., and Jacobsen E.N. J. Am. Chem. Soc. 125 (2003) 11204-11205
60. Hughes G., Kimura M., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 11253-11258
61. Brandau S., Landa A., Franzén J., Marigo M., and Jørgensen K.A. Angew. Chem., Int. Ed. 45 (2006) 4305-4309
62. Koech P.K., and Krische M.J. Tetrahedron 62 (2006) 10594-10602
63. Ito M., Sakaguchi A., Kobayashi C., and Ikariya T. J. Am. Chem. Soc. 129 (2007) 290-291
64. Bower J.F., Riis-Johannessen T., Szeto P., Whitehead A.J., and Gallagher T. Chem. Commun. (2007) 728-730
65. For examples of asymmetric syntheses of paroxetine, see:. Yu M.S., Lantos I., Peng Z.-Q., Yu J., and Cacchio T. Tetrahedron Lett. 41 (2000) 5647-5651
66. Amat M., Bosch J., Hidalgo J., Canto M., Perez M., Llor N., Molins E., Miravitlles C., Orozco M., and Luque J. J. Org. Chem. 65 (2000) 3074-3084
67. Johnson T.A., Curtis M.D., and Berk P. J. Am. Chem. Soc. 123 (2001) 1004-1005
68. Greenhalgh D.A., and Simpkins N.S. Synlett (2002) 2074-2076
69. Yamada S., and Jahan I. Tetrahedron Lett. 46 (2005) 8673-8676 and references cited therein
70. Evans D.A., Fu G.C., and Hoveyda A.H. J. Am. Chem. Soc. 114 (1992) 6671-6679
71. Enantiomeric excess was determined by HPLC analysis after protection of the secondary amine with a Boc group. See Supplementary data for detail.