Rhodium-catalyzed convenient synthesis of functionalized tetrahydronaphthalenes

Tetrahedron

Volumn 66, Issue 8, 2010, Pages 1563-1569

  Tanaka, Ken ^a   Sawada, Yayoi ^a   Aida, Yusuke ^a   Thammathevo, Maliny ^a   Tanaka, Rie ^a   Sagae, Hiromi ^a   Otake, Yousuke ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 HEPTADIYNE; 1,7 OCTADIYNE DERIVATIVE; 1,8 NONADIYNE; ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALKYNE DERIVATIVE; BISPHOSPHINE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODACYCLOPENTADIENE; RHODIUM; RHODIUM DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 74549163702     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.12.042     Document Type: Article

References (83)

1. For examples, see:
2. Cimetiere B., Dubuffet T., Landras C., Descombes J.-J., Simonet S., Verbeuren T.J., and Lavielle G. Bioorg. Med. Chem. Lett. 8 (1998) 1381
3. Dumas M., Dumas J.P., Bardou M., Rochette L., Advenier C., and Giudicelli J.F. Eur. J. Pharmacol. 348 (1998) 223
4. Stutz A., Georgopoulos A., Granitzer W., Petranyi G., and Berney D. J. Med. Chem. 29 (1986) 112
5. Beaumont D., and Waigh R.D. Prog. Med. Chem. 18 (1981) 45
6. For an example, see:. Amer I., Amer H., and Blum J. J. Mol. Catal. 34 (1986) 221
7. For an example, see:. Kurteva V.B., Santos A.G., and Afonso C.A.M. Org. Biomol. Chem. 2 (2004) 514
8. For recent reviews of transition-metal-catalyzed [2+2+2] cycloadditions, see:
9. Galan B.R., and Rovis T. Angew. Chem., Int. Ed. 48 (2009) 2830
10. Tanaka K. Chem. Asian J. 4 (2009) 508
11. Varela J.A., and Saá C. Synlett (2008) 2571
12. Shibata T., and Tsuchikama K. Org. Biomol. Chem. (2008) 1317
13. Heller B., and Hapke M. Chem. Soc. Rev. 36 (2007) 1085
14. Agenet N., Buisine O., Slowinski F., Gandon V., Aubert C., and Malacria M. In: RajanBabu T.V. (Ed). Organic Reactions Vol. 68 (2007), John Wiley, Hoboken 1
15. Chopade P.R., and Louie J. Adv. Synth. Catal. 348 (2006) 2307
16. Gandon V., Aubert C., and Malacria M. Chem. Commun. (2006) 2209
17. Kotha S., Brahmachary E., and Lahiri K. Eur. J. Org. Chem. (2005) 4741
18. Gandon V., Aubert C., and Malacria M. Curr. Org. Chem. 9 (2005) 1699
19. Yamamoto Y. Curr. Org. Chem. 9 (2005) 503
20. A gold-catalyzed benzannulation leading to tetrahydronaphthalenes was reported; see:. Grisé C.M., and Barriault L. Org. Lett. 8 (2006) 5905
21. Takai K., Yamada M., and Utimoto K. Chem. Lett. (1995) 851
22. Hara R., Guo Q., and Takahashi T. Chem. Lett. (2000) 140
23. Nishikawa T., Shinokubo H., and Oshima K. Tetrahedron 59 (2003) 9661
24. Gandon V., Leca D., Aechtner T., Vollhardt K.P.C., Malacria M., and Aubert C. Org. Lett. 6 (2004) 3405
25. Turek P., Kotora M., Tišlerová I., Hocek M., Votruba I., and Císařová I. J. Org. Chem. 69 (2004) 9224
26. Bhatarah P., and Smith E.H. J. Chem. Soc., Perkin Trans. 1 (1992) 2163
27. For [2+2+2] reactions of electron-deficient 1,7-octadiyne derivatives with 1,3-diynes at elevated temperature (80 °C), see:
28. Jeevanandam A., Korivi R.P., Huang I., and Cheng C.-H. Org. Lett. 4 (2002) 807 Under microwave heating, see:
29. Teske J.A., and Deiters A. J. Org. Chem. 73 (2008) 342
30. Although a single example of the nickel-catalyzed reaction between 1,7-octadiyne (1a) and a monoyne was reported, the yield was extremely low (13%); see:. Turek P., Novák P., Pohl R., Hocek M., and Kotora M. J. Org. Chem. 71 (2006) 8978
31. Palladium-catalyzed [2+2+2] cycloadditions of 1,7-octadiyne derivatives and 3,11-tridecadiyne with allylic compounds leading to substituted benzenes were reported; see:. Tsukada N., Sugawara S., Nakaoka K., and Inoue Y. J. Org. Chem. 68 (2003) 5961
32. For related discussions, see:
33. Yamamoto Y., Arakawa T., Ogawa R., and Itoh K. J. Am. Chem. Soc. 125 (2003) 12143
34. Grigg R., Scott R., and Stevenson P. J. Chem. Soc., Perkin Trans. 1 (1988) 1357
35. Beesley R.M., Ingold C.K., and Thorpe J.F. J. Chem. Soc. 107 (1915) 1080
36. Jung M.E., and Gervay J. J. Am. Chem. Soc. 113 (1991) 224
37. Tanaka K., and Shirasaka K. Org. Lett. 5 (2003) 4697
38. Tanaka K., Toyoda K., Wada A., Shirasaka K., and Hirano M. Chem.- Eur. J. 11 (2005) 1145
39. For our accounts, see:
40. Tanaka K. Synlett (2007) 1977
41. Tanaka K., Nishida G., and Suda T. J. Synth. Org. Chem. Jpn. 65 (2007) 862
42. For a review of rhodium-catalyzed cyclotrimerization reactions, see:. Fujiwara M., and Ojima I. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim 129
43. Kondoh A., Yorimitsu H., and Oshima K. J. Am. Chem. Soc. 129 (2007) 6996
44. Doherty S., Knight J.G., Smyth C.H., Harrington R.W., and Clegg W. Org. Lett. 9 (2007) 4925
45. Doherty S., Smyth C.H., Harrington R.W., and Clegg W. Organometallics 27 (2008) 4837
46. 2-Tetrahydronaphthoyl derivatives are found in various pharmaceutical ingredients.For selected examples see:
47. Ujihara, K.; Ujita, S.; Manabe, A.; Takaishi, M. WO 2,009,075,250 A1, 2009;
48. Chem. Abstr. 151 (2009) 50508
49. Umemiya, H.; Takahashi, M.; Bohno, M.; Kawabe, K.; Shirokawa, S.; Nagatsuka, T.; Sasako, S.; Satou, R.; Itoh, S.; Shimizu, T. WO 2,009,011,285 A1, 2009;
50. Chem. Abstr. 150 (2009) 168384
51. Ogino, M.; Nakada, Y.; Shimada, M.; Asano, K.; Tamura, N.; Masago, M. WO 2,006,082,952 A1, 2006;
52. Chem. Abstr. 145 (2006) 230632
53. 2-Tetrahydronaphthalenemethanol derivatives are found in various pharmaceutical ingredients.For selected examples see:
54. Brown, S.P.; Dransfield, P.; Houze, J.B.; Liu, J.; Liu, J.; Ma, Z.; Medina, J.C.; Pattaropong, V.; Schmitt, M.J.; Sharma, R.; Wang, Y. WO 2,008,030,618 A1, 2008;
55. Chem. Abstr. 148 (2008) 355798
56. Salama I., Hocke C., Utz W., Prante O., Boeckler F., Huebner H., Kuwert T., and Gmeiner P. J. Med. Chem. 50 (2007) 489
57. Stolle, A.; Antonicek, H.-P.; Lensky, S.; Voerste, A.; Muller, T.; Baumgarten, J.; Von Dem Bruch, K.; Muller, G.; Stropp, U.; Horvath, E.; De Vry, J.-M.-V.; Schreiber, R. WO 2,001,004,107 A1, 2001;
58. Chem. Abstr. 134 (2001) 115845
59. Padwa A., and Wong G.S.K. J. Org. Chem. 51 (1986) 3125
60. For examples of the metal-catalyzed sequential [2+2+2] cycloaddition and lactonization, see:
61. Tanaka K., Osaka T., Noguchi K., and Hirano M. Org. Lett. 9 (2007) 1307
62. Chang H.-T., Jeganmohan M., and Cheng C.-H. Chem. Commun. (2005) 4955
63. Takeuchi R., and Nakaya Y. Org. Lett. 5 (2003) 3659
64. Dieck T.H., Munz C., and Müller C. J. Organomet. Chem. 384 (1990) 243
65. Abdulla K., Booth B.L., and Stacey C. J. Organomet. Chem. 293 (1985) 103
66. Ref. 10b. For synthesis of tetralin lactones by ruthenium-catalyzed [2+2+2] cycloaddition using alkynylboronates followed by palladium-catalyzed carbonylation, see:
67. Yamamoto Y., Ishii J.-i., Nishiyama H., and Itoh K. J. Am. Chem. Soc. 127 (2005) 9625
68. 2-Tetrahydronaphthalenemethylamine derivatives are found in various pharmaceutical ingredients.For selected examples see:
69. Fyfe, M.C.T.; Gattrell, W.; Sambrook-Smith, C.P. WO 2,009,050,523 A1, 2009;
70. Chem. Abstr. 150 (2009) 447956
71. Beavers, L.S.; Gadski, R.A.; Hipskind, P.A.; Jesudason, C.D.; Lindsley, C.W.; Lobb, K.L.; Pickard, R.T. WO 2,005,082,893 A2, 2005;
72. Chem. Abstr. 143 (2005) 266686
73. Underwood D.J., Green B.G., Chabin R., Mills S., Doherty J.B., Finke P.E., MacCoss M., Shah S.K., Burgey C.S., Dickinson T.A., Griffin P.R., Lee T.E., Swiderek K.M., Covey T., Westler W.M., and Knight W.B. Biochemistry 34 (1995) 14344
74. For examples using a stoichiometric amount of metal complexes, see:
75. Gerardus B.M., Kostermans W.H., and De Wolf F.B. Tetrahedron 43 (1987) 2955
76. Ref. 9.
77. For an example using a catalytic amount of a cobalt complex, see:. Vitulli G., Bertozzi S., Lazzaroni R., and Salvadori P. J. Mol. Catal. 45 (1988) 155
78. Marvell E.N., Hilton C., and Cleary M. J. Org. Chem. 48 (1983) 4272
79. von Zezschwitz P., Petry F., and de Meijere A. Chem.- Eur. J. 7 (2001) 4035
80. von Essen R., Frank D., Sünnemann H.W., Vidovic D., Magull J., and de Meijere A. Chem.- Eur. J. 11 (2005) 6583
81. Neudeck H.K. Monatsh. Chem. 120 (1989) 597
82. Maier G., Wilmes R., Fuchs H., and Leinweber M. Chem. Ber. 126 (1993) 1827
83. Cho C.S., Patel D.B., and Shim S.C. Tetrahedron 61 (2005) 9490