Asymmetric intramolecular Pd(II)-catalysed amidocarbonylation of unsaturated amino alcohols

Tetrahedron Asymmetry

Volumn 20, Issue 23, 2009, Pages 2720-2723

  Koóš, Peter ^a   Špánik, Ivan ^a   Gracza, Tibor ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXA 6 AZABICYCLO[3.3.0]OCTAN 3 ONE DERIVATIVE; ACETIC ACID; AMINOALCOHOL; BENZOQUINONE; CARBON MONOXIDE; N PROTECTED 1 AMINO PENT 4 ENE 3 OL DERIVATIVE; OCTANE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; KINETICS; PRIORITY JOURNAL;

EID: 76449096964     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.10.024     Document Type: Article

References (75)

1. For reviews see:. Colquhoun H.M., Thompson D.J., and Twigg M.V. Carbonylation (1991), Plenum Press, New York
2. Tsuji J. Palladium Reagents and Catalysts: New Perspective for the 21st Century (2004), John Wiley & Sons, Chichester
3. Schmalz H.G., and Geis O. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Syntheses Vol. 2 (2002), John Wiley & Sons, New York 2397
4. Muzart J. Tetrahedron 61 (2005) 5955-6008
5. Muzart J. Tetrahedron 61 (2005) 9423-9463
6. Gracza T., Hasenöhrl T., Stahl U., and Jäger V. Synthesis (1991) 1108-1118
7. Jäger V., Gracza T., Dubois E., Hasenöhrl T., Hümmer W., Kautz U., Kirschbaum B., Lieberknecht A., Remen L., Shaw D., Stahl U., and Stephan O. In: Helmchen G., Dibo J., Flubacher D., and Wiese B. (Eds). Pd(II)-Catalyzed Carbonylation of Unsaturated Polyols and Aminopolyols. Organic Synthesis via Organometallics OSM 5 (1997), Vieweg, Braunschweig 331-360
8. Tamaru Y., Kobayshi T., Kawamura S., Ochiai H., and Yoshida Z. Tetrahedron Lett. 26 (1985) 4479-4482
9. Tamaru Y., Hojo M., Higashimura H., and Yoshida Z. J. Am. Chem. Soc. 110 (1988) 3994-4002
10. Tamaru Y., and Kimura M. Synlett (1997) 749-757
11. Tamaru Y., Hojo M., and Yoshida Z. J. Org. Chem. 53 (1988) 5731-5741
12. Takahata H., Banba Y., and Momose T. Tetrahedron: Asymmetry 2 (1991) 445-448
13. Hümmer W., Dubois E., Gracza T., and Jäger V. Synthesis (1997) 634-642
14. Szolcsányi P., Gracza T., Koman M., Pronayová N., and Liptaj T. Chem. Commun. (2000) 471-472
15. Szolcsányi P., Gracza T., Koman M., Pronayová N., and Liptaj T. Tetrahedron: Asymmetry (2000) 2579-2597
16. Koman M., Szolcsányi P., and Gracza T. Acta Crystallogr., Sect. C 56 (2000) e138
17. Szolcsányi P., Gracza T., and Spánik I. Tetrahedron Lett. 49 (2008) 1357-1360
18. Geissman T.A., and Waiss Jr. A.C. J. Org. Chem. 27 (1962) 139-142
19. For synthesis of related structures see, for example,. Casiraghi G., Zanardi F., Rassu G., and Pinna L. Org. Prep. Proced. Int. 28 (1996) 641-690
20. Hartmann T., and Witte L. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives (1995), Pergamon Press, New York 155-223
21. Mattocks A.R. Chemistry and Toxicology of Pyrrolizidine Alkaloids (1986), Academic, London
22. Niwa H., Okamoto O., Miyachi Y., Uosaki Y., and Yamada K. J. Org. Chem. 52 (1987) 2941-2943
23. Nagao Y., Dai W.-M., Ochiai M., and Shiro M. J. Org. Chem. 54 (1989) 5211-5217
24. Wee A.G.H. J. Org. Chem. 66 (2001) 8513-8517
25. Clark-Lewis J.W., and Mortimer P.I. J. Chem. Soc. (1960) 189-194
26. Pandey G., and Lakshmaiah G. Synlett (1994) 277-278
27. Rüeger H., and Benn M. Heterocycles 20 (1983) 1331-1334
28. Rüeger H., and Benn M. Heterocycles 19 (1982) 23-25
29. Buchanan J.G., Jigajinni V.B., Singh G., and Wightman R.H. J. Chem. Soc., Perkin Trans. 1 (1987) 2377-2384
30. Buchanan J.G., Singh G., and Wightman R.H. J. Chem. Soc., Chem. Commun. (1984) 1299-1300
31. Nishimura Y., Kondo S., and Umezawa H. J. Org. Chem. 50 (1985) 5210-5214
32. Thaning M., and Wistrand L.-G. J. Org. Chem. 55 (1990) 1406-1408
33. Niwa H., Miyachi Y., Okamoto O., Uosaki Y., Kuroda A., Ishiwata H., and Yamada K. Tetrahedron 48 (1992) 393-412
34. Shishido K., Sukegawa Y., Fukumoto K., and Kametani T. J. Chem. Soc., Perkin Trans. 1 (1987) 993-1004
35. Chamberlin A.R., and Chung J.Y.L. J. Org. Chem. 50 (1985) 4425-4431
36. Kametani T., Yukawa H., and Honda T. J. Chem. Soc., Chem. Commun. (1988) 685-687
37. Cooper J., Gallagher P.T., and Knight D.W. J. Chem. Soc., Perkin Trans. 1 (1993) 1313-1317
38. Cooper J., Gallagher P.T., and Knight D.W. J. Chem. Soc., Chem. Commun. (1988) 509-510
39. Paolucci C., Venturelli F., and Fava A. Tetrahedron Lett. 36 (1995) 8127-8128
40. Kouyama T., Matsunaga H., Ishizuka T., and Kunieda T. Heterocycles 44 (1997) 479-486
41. Miranda P.C.M.L., and Correia C.R.D. Tetrahedron Lett. 40 (1999) 7735-7738
42. Ohtake H., Imada Y., and Murahashi S.-I. Bull. Chem. Soc. Jpn. 72 (1999) 2737-2754
43. Huang J.-M., Hong S.-C., Wu K.-L., and Tsai Y.-M. Tetrahedron Lett. 45 (2004) 3047-3050
44. Du J.-X., Huang H.-Y., and Huang P.-Q. Tetrahedron: Asymmetry 15 (2004) 3461-3466
45. Kato K., Tanaka M., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 1511-1513
46. Kato K., Tanaka M., Yamamura S., Yamamoto Y., and Akita H. Tetrahedron Lett. 44 (2003) 3089-3092
47. Kato K., Matsuba C., Kusakabe T., Takayama H., Yamamura S., Mochida T., Akita H., Peganova T.A., Vologdin N.V., and Gusev O.V. Tetrahedron 62 (2006) 9988-9999
48. Uozumi Y., Kato K., and Hayashi T. J. Am. Chem. Soc. 119 (1997) 5063-5064
49. Uozumi Y., Kato K., and Hayashi T. J. Org. Chem. 63 (1998) 5071-5075
50. Uozumi Y., Kyota H., Kato K., Ogasawara M., and Hayashi T. J. Org. Chem. 64 (1999) 1620-1625
51. Wang F., Zhang Y.J., Wei H., Zhang J., and Zhang W. Tetrahedron Lett. 48 (2007) 4083-4086
52. Wang F., Zhang Y.J., Yang G., and Zhang W. Tetrahedron Lett. 48 (2007) 4179-4182
53. Trend R.M., Ramtohul Y.K., Ferreira E.M., and Stoltz B.M. Angew. Chem., Int. Ed. 42 (2003) 2892-2895
54. Trend R.M., Ramtohul Y.K., and Stoltz B. J. Am. Chem. Soc. 127 (2005) 17778-17788
55. Arai M.A., Kuraishi M., Arai T., and Sasai H. J. Am. Chem. Soc. 123 (2001) 2907-2908
56. Koranne P.S., Tsujihara T., Arai M.A., Bajracharya G.B., Suzuki T., Onitsuka K., and Sasai H. Tetrahedron: Asymmetry 18 (2007) 919-923
57. Arai M.A., Arai T., and Sasai H. Org. Lett. 1 (1999) 1795-1979
58. Shinohara T., Arai M.A., Wakita K., Arai T., and Sasai H. Tetrahedron Lett. 44 (2003) 711-714
59. Kapitán P., and Gracza T. ARKIVOC viii (2008) 8-17
60. Kapitán P., and Gracza T. Tetrahedron: Asymmetry 19 (2008) 38-44
61. Itoh T., Mitsukura K., Kanphai W., Takagi Y., Kihara H., and Tsukube H. J. Org. Chem. 62 (1997) 9165-9176
62. Takahata H., Tamija M., Banba Y., and Momose T. Chem. Pharm. Bull. 37 (1989) 2550-2552
63. Das N.B., and Torssell K.B.G. Tetrahedron 39 (1983) 2247-2253
64. Tamaru Y., Kawamura S., Tanaka K., and Yoshida Z. Tetrahedron Lett. 25 (1984) 1063-1066
65. Evans P.A., Holmes A.B., and Russell K. J. Chem. Soc., Perkin Trans. 1 (1994) 3397-3409
66. Jäger V., Hümmer W., Stahl U., and Gracza T. Synthesis (1991) 769-776
67. Ewing W.R., Harris B.D., Bhat K.L., and Joullie M.M. Tetrahedron 42 (1986) 2421-2428
68. Knight D.W., Share A.C., and Gallagher P.T. J. Chem. Soc., Perkin Trans. 1 (1997) 2089-2097
69. Bisoxazoline ligands D, E, were synthesised by the described procedures; see:. Müller D., Umbricht G., Weber B., and Pfaltz A. Helv. Chim. Acta 74 (1991) 232-240
70. Ligand H was purchased from Dr. Radovan Šebesta, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynska dolina CH2, Bratislava, Slovakia.
71. Wee A.G.H. Tetrahedron Lett. 41 (2000) 9025-9029
72. Luna A., Gutiérrez M.-C., Furstoss R., and Alphand V. Tetrahedron: Asymmetry 16 (2005) 2521-2524
73. Murahashi S.-I., Ohtake H., and Imada Y. Tetrahedron Lett. 39 (1998) 2765-2766
74. Barco A., Baricordi N., Benetti S., Risi C.D., Polini G.P., and Zanirato V. Tetrahedron 63 (2007) 4278-4283
75. Honda T., and Matsumoto S. Heterocycles 66 (2005) 341-346