Stereoselective synthesis of 3-substituted tetrahydroisoquinolines from phthalan and chiral N-sulfinylimines

Tetrahedron Letters

Volumn 50, Issue 33, 2009, Pages 4710-4713

  García, Daniel ^a   Moreno, Benjamín ^a   Soler, Tatiana ^a   Foubelo, Francisco ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Chiral sulfinylimines; Diastereoselective addition; DTBB catalysed lithiation; Organozincates; Phthalan; Reductive ring opening

Indexed keywords

AMINOALCOHOL; CHLORIDE; CHLOROFORM; HYDROCHLORIC ACID; IMINE; LITHIUM; METHANOL; PHTHALIDE DERIVATIVE; SODIUM HYDROXIDE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HYDROLYSIS; RING OPENING; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 67649372526     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.010     Document Type: Article

References (91)

1. For a review, see:. Scott J.D., and Williams R.M. Chem. Rev. 102 (2002) 1669-1730
2. For reviews, see:. Vicario J.L., Badia D., Carrillo L., and Etxebarria J. Curr. Org. Chem. 7 (2003) 1775-1792
3. Bracca A.B.J., and Kaufman T.S. Tetrahedron 60 (2004) 10575-10610
4. Siengalewicz P., Rinner U., and Mulzer J. Chem. Soc. Rev. 37 (2008) 2676-2690
5. Liu G., Cogan D.A., and Ellman J.A. J. Am. Chem. Soc. 119 (1997) 9913-9914
6. Cogan D.A., Liu G., and Ellman J.A. Tetrahedron 55 (1999) 8883-8904
7. Davis F.A., and McCoull W. J. Org. Chem. 64 (1999) 3396-3397
8. McMahon J.P., and Ellman J.A. Org. Lett. 6 (2004) 1645-1647
9. Lu B.Z., Senanayake C., Li N., Han Z., Bakale R.P., and Wald S.A. Org. Lett. 7 (2005) 2599-2602
10. Dirscherl G., Rooshenas P., Schreiner P.R., Lamaty F., and König B. Tetrahedron 64 (2008) 3005-3016
11. Cogan D.A., and Ellman J.A. J. Am. Chem. Soc. 121 (1999) 268-269
12. Cogan D.A., Liu G., and Ellman J. Tetrahedron 55 (1999) 8883-8904
13. Davis F.A., Melamed J.Y., and Sharik S.S. J. Org. Chem. 71 (2006) 8761-8766
14. Chemla F., and Ferreira F. J. Org. Chem. 69 (2004) 8244-8250
15. Chemla F., and Ferreira F. Synlett (2004) 983-986
16. Ferreira F., Audouin M., and Chemla F. Chem. Eur. J. 11 (2005) 5269-5278
17. Chemla F., and Ferreira F. Synlett (2006) 2613-2616
18. Sun X.-W., Xu M.-H., and Lin G.-Q. Org. Lett. 8 (2006) 4979-4982
19. Kolodney G., Sklute G., Perrone S., Knochel P., and Marek I. Angew. Chem., Int. Ed. 46 (2007) 9291-9294
20. Chemla F., Ferreira F., Gaucher X., and Palais L. Synthesis (2007) 1235-1241
21. Voituriez A., Pérez-Luna A., Ferreira F., Botuha C., and Chemla F. Org. Lett. 11 (2009) 931-934
22. Foubelo F., and Yus M. Tetrahedron: Asymmetry 15 (2004) 3823-3825
23. Wang Z.-Q., Feng C.-Q., Xu M.-H., and Lin G.-Q. J. Am. Chem. Soc. 129 (2007) 5336-5337
24. Sun X.-W., Liu M., Xu M.-H., and Lin G.-Q. Org. Lett. 10 (2008) 1259-1262
25. González-Gómez J.C., Foubelo F., and Yus M. Synlett (2008) 2777-2780
26. Medjahdi M., González-Gómez J.C., Foubelo F., and Yus M. Heterocycles 76 (2008) 569-581
27. For reviews, see:. Davis F.A., Zhou P., and Chen B.-C. Chem. Soc. Rev. 27 (1998) 13-18
28. Ellman J.A., Owens T.D., and Tang T.P. Acc. Chem. Res. 35 (2002) 984-995
29. Ellman J.A. Pure Appl. Chem. 75 (2003) 39-46
30. Zhou P., Chen B.-C., and Davis F.A. Tetrahedron 60 (2004) 8003-8030
31. Morton D., and Stockman R.A. Tetrahedron 62 (2006) 8869-8905
32. Lin G.-Q., Xu M.-H., Zhong Y.-W., and Sun X.-W. Acc. Chem. Res. 41 (2008) 831-840
33. Ferreira F., Botuha C., Chemla F., and Pérez-Luna A. Chem. Soc. Rev. 38 (2009) 1162-1186
34. Weix D.J., and Ellman J.A. Org. Lett. 5 (2003) 1317-1320
35. Weix D.J., and Ellman J.A. Org. Synth. 82 (2005) 157-165
36. Wakayama M., and Ellman J.A. J. Org. Chem. 74 (2009) 2646-2650
37. Aggarwal V.K., Barbero N., McGarrigle E.M., Mickle G., Navas R., Suárez J.R., Unthank M.G., and Yar M. Tetrahedron Lett. 50 (2009) 3482-3484
38. For reviews on functionalised organolithium compounds, see:. Nájera C., and Yus M. Trends Org. Chem. 2 (1991) 155-181
39. Nájera C., and Yus M. Org. Prep. Proc. Int. 27 (1995) 383-457
40. Nájera C., and Yus M. Recent Res. Dev. Org. Chem. 1 (1997) 67-96
41. Yus M., and Foubelo F. Rev. Heteroatom Chem. 17 (1997) 73-107
42. Nájera C., and Yus M. Curr. Org. Chem. 7 (2003) 867-926
43. Nájera C., Sansano J.M., and Yus M. Tetrahedron 59 (2003) 9255-9303
44. Chinchilla R., Nájera C., and Yus M. Chem. Rev. 104 (2004) 2667-2722
45. Chinchilla R., Nájera C., and Yus M. Tetrahedron 61 (2005) 3139-3176
46. See also the special issue of Tetrahedron Symposium in Print (Eds.: Nájera, C; Yus, M.) devoted to 'Functionalised Organolithium Compounds', Tetrahedron 2005, 61, issue no. 13.
47. Yus M., and Foubelo F. In: Knochel P. (Ed). Handbook of Functionalized Organometallics (2005), Wiley-VCH, Weinheim Chapter 2
48. Foubelo F., and Yus M. Chem. Soc. Rev. 37 (2008) 2620-2633
49. For reviews, see:. Yus M., and Foubelo F. Rev. Heteroatom Chem. 17 (1997) 73-107
50. Yus M., and Foubelo F. In: Attanasi O.A., and Spinelli D. (Eds). Targets in Heterocyclic Systems (2002), Italian Society of Chemistry, Rome 136-171
51. Yus M. Pure Appl. Chem. 75 (2003) 1453-1475
52. Yus M., and Foubelo F. Adv. Heterocycl. Chem. 91 (2006) 135-158
53. For reviews, see:. Yus M. Chem. Soc. Rev. 25 (1996) 155-161
54. Ramón D.J., and Yus M. Eur. J. Org. Chem. (2000) 225-237
55. Yus M. Synlett (2001) 1197-1205
56. Yus M., and Ramón D.J. Lat. J. Chem. (2002) 79-92
57. Ramón D.J., and Yus M. Rev. Cubana Quim. 14 (2002) 75-115
58. Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 1 (2004), John Wiley & Sons, Chichester Part 2, Chapter 11
59. Almena J., Foubelo F., and Yus M. Tetrahedron 51 (1995) 3351-3364
60. Soler T., Bachki A., Falvello L.R., Foubelo F., and Yus M. Tetrahedron: Asymmetry 9 (1998) 3939-3943
61. Soler T., Bachki A., Falvello L.R., Foubelo F., and Yus M. Tetrahedron: Asymmetry 11 (2000) 493-517
62. Falvello L.R., Foubelo F., Soler T., and Yus M. Tetrahedron: Asymmetry 11 (2000) 2063-2066
63. Foubelo F., Soler T., and Yus M. Tetrahedron: Asymmetry 12 (2001) 801-810
64. Foubelo F., Gómez C., Gutiérrez A., and Yus M. J. Heterocycl. Chem. 37 (2000) 1061-1064
65. Pastor I.M., and Yus M. Tetrahedron Lett. 41 (2000) 1589-1592
66. Pastor I.M., and Yus M. Tetrahedron 57 (2001) 2371-2378
67. Yus M., and Gomis J. Tetrahedron Lett. 42 (2001) 5721-5724
68. Yus M., and Gomis J. Eur. J. Org. Chem. (2002) 1989-1995
69. Yus M., and Gomis J. Eur. J. Org. Chem. (2003) 2043-2048
70. Azzena U., Demartis S., and Melloni G. J. Org. Chem. 61 (1996) 4913-4919
71. Foubelo F., García D., Moreno B., and Yus M. Tetrahedron Lett. 48 (2007) 3379-3383
72. García D., Foubelo F., and Yus M. Tetrahedron 64 (2008) 4275-4286
73. García Ruano J.L., Carreño M.C., Toledo M.A., Aguirre J.M., Aranda M.T., and Fischer J. Angew. Chem., Int. Ed. 39 (2000) 2736-2737
74. García Ruano J.L., Alemán J., and Soriano J.F. Org. Lett. 5 (2003) 677-680
75. García Ruano J.L., and Alemán J. Org. Lett. 5 (2003) 4513-4516
76. García Ruano J.L., Aranda M.T., and Aguirre J.M. Tetrahedron 60 (2004) 5383-5392
77. Arroyo Y., Meana A., Rodríguez J.F., Santos M., Sanz-Tejedor M.A., and García Ruano J.L. J. Org. Chem. 70 (2005) 3914-3920
78. García Ruano J.L., Alemán J., and Parra A. J. Am. Chem. Soc. 127 (2005) 13048-13054
79. García Ruano J.L., Alemán J., and Cid M.B. Synthesis (2006) 687-691
80. Arroyo Y., Rodríguez J.F., Santos M., Sanz Tejedor M.A., and García Ruano J.L. J. Org. Chem. 72 (2007) 1035-1038
81. Arroyo Y., Meana A., Sanz Tejedor M.A., Alonso I., and García Ruano J.L. J. Org. Chem. 74 (2009) 764-772
82. See, for instance:. Liu G., Cogan D.A., Owens T.D., Tang T.P., and Ellman J.A. J. Org. Chem. 64 (1999) 1278-1284
83. Almansa R., Guijarro D., and Yus M. Tetrahedron: Asymmetry 19 (2008) 603-606
84. Almansa R., Guijarro D., and Yus M. Tetrahedron: Asymmetry 19 (2008) 2484-2491
85. +.
86. o).
87. Bharatam P.V., Amita, and Kaur D. J. Phys. Org. Chem. 15 (2002) 197-203
88. Bharatam P.V., Uppal P., Amita, and Kaur D. J. Chem. Soc. Perkin Trans. 2 (2000) 43-50
89. 15N requires 209.1204.
90. shelx97 [includes shelxs97, shelxl97 and ciftab]-Programs for Crystal Structure Analysis (Release 97-2). Sheldrick, G. M., Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.
91. Enders D., Braig V., Boudou M., and Raabe G. Synthesis (2004) 2980-2990