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Volumn , Issue 15, 2010, Pages 2893-2903

Reductive ring-opening of phthalan and isochroman: Application to the stereoselective synthesis of tetrahydroisoquinolines and tetrahydrobenzazepines

(3) García, Daniel a Foubelo, Francisco a Yus, Miguel a

a UNIVERSITY OF ALICANTE (Spain)

Author keywords

Diastereoselectivity; Hydrolysis; Lithiation; Lithium; Nitrogen heterocycles; Sulfinylimines; Zincates

Indexed keywords

EID: 77952176488 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.201000111 Document Type: Article

Times cited : (20)

References (64)

1
- 0037687811
- For recent reviews on functionalised organolithium compounds, see: a) C. Nájera, M. Yus, Curr. Org. Chem. 2003, 7, 867-926;
- (2003) Curr. Org. Chem. , vol.7 , pp. 867-926
- Nájera, C.¹ Yus, M.²

2
- 0242352416
- b) C. Nájera, J. M. Sansano, M. Yus, Tetrahedron 2003, 59, 9255-9303;
- (2003) Tetrahedron , vol.59 , pp. 9255-9303
- Nájera, C.¹ Sansano, J.M.² Yus, M.³

3
- 2942530950
- c) R. Chinchilla, C. Nájera, M. Yus, Chem. Rev. 2004, 104, 2667-2722;
- (2004) Chem. Rev. , vol.104 , pp. 2667-2722
- Chinchilla, R.¹ Nájera, C.² Yus, M.³

4
- 14844291428
- d) R. Chinchilla, C. Nájera, M. Yus, Tetrahedron 2005, 61, 3139-3176;
- (2005) Tetrahedron , vol.61 , pp. 3139-3176
- Chinchilla, R.¹ Nájera, C.² Yus, M.³

5
- 56549084564
- e) F. Foubelo, M. Yus, Chem. Soc. Rev. 2008, 37, 2620-2633.
- (2008) Chem. Soc. Rev. , vol.37 , pp. 2620-2633
- Foubelo, F.¹ Yus, M.²

6
- 0003961355
- Pergamon Press, Oxford
- For a monograph, see: J. Clayden, in: Organolithiums: Selectivity for Synthesis, Pergamon Press, Oxford, 2002.
- (2002) Organolithiums: Selectivity for Synthesis
- Clayden, J.¹

7
- 0141988919
- For recent reviews, see: a) M. Yus, Pure Appl. Chem. 2003, 75, 1453-1475;
- (2003) Pure Appl. Chem. , vol.75 , pp. 1453-1475
- Yus, M.¹

8
- 33745418080
- b) M. Yus, F. Foubelo, Adv. Heterocycl. Chem. 2006, 91, 135-158.
- (2006) Adv. Heterocycl. Chem. , vol.91 , pp. 135-158
- Yus, M.¹ Foubelo, F.²

9
- 34147153184
- For the last papers on this topic from our laboratory, see: a) F. Foubelo, D. Garcia, B. Moreno, M. Yus, Tetrahedron Lett. 2007, 48, 3379-3383;
- (2007) Tetrahedron Lett. , vol.48 , pp. 3379-3383
- Foubelo, F.¹ Garcia, D.² Moreno, B.³ Yus, M.⁴

10
- 40749114051
- b) D. Garcia, F. Foubelo, M. Yus, Heterocycles 2007, 74, 507-519;
- (2007) Heterocycles , vol.74 , pp. 507-519
- Garcia, D.¹ Foubelo, F.² Yus, M.³

11
- 41549162312
- c) D. Garcia, F. Foubelo, M. Yus, Tetrahedron 2008, 64, 4275-4286;
- (2008) Tetrahedron , vol.64 , pp. 4275-4286
- Garcia, D.¹ Foubelo, F.² Yus, M.³

12
- 77952179619
- d) D. Garcia, F. Foubelo, M. Yus, Heterocycles 2009, 11, 991-1005.
- (2009) Heterocycles , vol.11 , pp. 991-1005
- Garcia, D.¹ Foubelo, F.² Yus, M.³

13
- 33746272630
- For recent mechanistic studies, see: a) C. Melero, A. Guijarro, M. Yus, Tetrahedron Lett. 2006, 47, 6267-6271;
- (2006) Tetrahedron Lett. , vol.47 , pp. 6267-6271
- Melero, C.¹ Guijarro, A.² Yus, M.³

14
- 34247895389
- b) C. Melero, H. Pérez, A. Guijarro, M. Yus, Tetrahedron Lett. 2007, 48, 4105-4109;
- (2007) Tetrahedron Lett. , vol.48 , pp. 4105-4109
- Melero, C.¹ Pérez, H.² Guijarro, A.³ Yus, M.⁴

15
- 36349021382
- c) C. Melero, A. Guijarro, V. Baumann, A. J. PérezJiménez, M. Yus, Eur. J. Org. Chem. 2007, 5514-5526;
- (2007) Eur. J. Org. Chem. , pp. 5514-5526
- Melero, C.¹ Guijarro, A.² Baumann, V.³ Pérezjiménez, A.J.⁴ Yus, M.⁵

16
- 38049098721
- d) C. Melero, R. P. Herrera, A. Guijarro, M. Yus, Chem. Eur. J. 2007, 13, 10096-10107;
- (2007) Chem. Eur. J. , vol.13 , pp. 10096-10107
- Melero, C.¹ Herrera, R.P.² Guijarro, A.³ Yus, M.⁴

17
- 77952127789
- e) H. Pérez C. Melero, A. Guijarro, M. Yus, Tetrahedron 2009, 65, 10764-10783.
- (2009) Tetrahedron , vol.65 , pp. 10764-10783
- Pérez, H.¹ Melero, C.² Guijarro, A.³ Yus, M.⁴

18
- 23244458679
- (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester
- For a recent review, see: M. Yus in The Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2004, vol.1, pp. 647-747.
- (2004) The Chemistry of Organolithium Compounds , vol.1 , pp. 647-747
- Yus, M.¹

19
- 0028947968
- a) J. Almena, F. Foubelo, M. Yus, Tetrahedron 1995, 57, 3351-3364;
- (1995) Tetrahedron , vol.57 , pp. 3351-3364
- Almena, J.¹ Foubelo, F.² Yus, M.³

20
- 77952226326
- b) U. Azzena, S. Demartis, M. G. Fiori, G. Melloni, L. Pisano, Tetrahedron Lett. 1995, 36, 8213-8216.
- (1995) Tetrahedron Lett. , vol.36 , pp. 8213-8216
- Azzena, U.¹ Demartis, S.² Fiori, M.G.³ Melloni, G.⁴ Pisano, L.⁵

21
- 0028963397
- J. Almena, F. Foubelo, M. Yus, Tetrahedron 1995, 57, 3365-3374.
- (1995) Tetrahedron , vol.57 , pp. 3365-3374
- Almena, J.¹ Foubelo, F.² Yus, M.³

22
- 0034635617
- a) T. Soler, A. Bachki, L. R. Falvello, F. Foubelo, M. Yus, Tetrahedron: Asymmetry 2000, 11, 493-517;
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 493-517
- Soler, T.¹ Bachki, A.² Falvello, L.R.³ Foubelo, F.⁴ Yus, M.⁵

23
- 0034595691
- b) L. R. Falvello, F. Foubelo, T. Soler, M. Yus, Tetrahedron: Asymmetry 2000, 11, 2063-2066;
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 2063-2066
- Falvello, L.R.¹ Foubelo, F.² Soler, T.³ Yus, M.⁴

24
- 0005183711
- c) F. Foubelo, T. Soler, M. Yus, Tetrahedron: Asymmetry 2001, 72, 801-810.
- (2001) Tetrahedron: Asymmetry , vol.72 , pp. 801-810
- Foubelo, F.¹ Soler, T.² Yus, M.³

25
- 0034603432
- a) I. Pastor, M. Yus, Tetrahedron Lett. 2000, 41, 1589-1592;
- (2000) Tetrahedron Lett. , vol.41 , pp. 1589-1592
- Pastor, I.¹ Yus, M.²

26
- 0035901357
- b) I. Pastor, M. Yus, Tetrahedron 2001, 57, 2371-2378.
- (2001) Tetrahedron , vol.57 , pp. 2371-2378
- Pastor, I.¹ Yus, M.²

27
- 0035855301
- a) M. Yus, J. Gomis, Tetrahedron Lett. 2001, 42, 5721-5724;
- (2001) Tetrahedron Lett. , vol.42 , pp. 5721-5724
- Yus, M.¹ Gomis, J.²

28
- 0036087846
- b) M. Yus, J. Gomis, Eur. J. Org. Chem. 2002, 1989-1995.
- (2002) Eur. J. Org. Chem. , pp. 1989-1995
- Yus, M.¹ Gomis, J.²

29
- 0038170220
- M. Yus, J. Gomis, Eur. J. Org. Chem. 2003, 2043-2048.
- (2003) Eur. J. Org. Chem. , pp. 2043-2048
- Yus, M.¹ Gomis, J.²

30
- 67649372526
- For a preliminary report, see: D. Garcia, B. Moreno, T. Soler, F. Foubelo, M. Yus, Tetrahedron Lett. 2009, 50, 4710-4713.
- (2009) Tetrahedron Lett. , vol.50 , pp. 4710-4713
- Garcia, D.¹ Moreno, B.² Soler, T.³ Foubelo, F.⁴ Yus, M.⁵

31
- 0032358630
- For reviews, see: a) F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18;
- (1998) Chem. Soc. Rev. , vol.27 , pp. 13-18
- Davis, F.A.¹ Zhou, P.² Chen, B.-C.³

32
- 0036851670
- b) J. A. Ellman, T. D. Owens, T. P. Tang, Acc. Chem. Res. 2002, 35, 984-995;
- (2002) Acc. Chem. Res. , vol.35 , pp. 984-995
- Ellman, J.A.¹ Owens, T.D.² Tang, T.P.³

33
- 0037223313
- c) J. A. Ellman, Pure Appl. Chem. 2003, 75, 39-46;
- (2003) Pure Appl. Chem. , vol.75 , pp. 39-46
- Ellman, J.A.¹

34
- 4143050401
- d) P. Zhou, B.-C. Chen, F. A. Davis, Tetrahedron 2004, 60, 8003-8030;
- (2004) Tetrahedron , vol.60 , pp. 8003-8030
- Zhou, P.¹ Chen, B.-C.² Davis, F.A.³

35
- 33747113614
- e) D. Morton, R. A. Stockman, Tetrahedron 2006, 62, 8869-8905;
- (2006) Tetrahedron , vol.62 , pp. 8869-8905
- Morton, D.¹ Stockman, R.A.²

36
- 49149123060
- f) G.-Q. Lin, M.H. Xu, Y-W Zhong, X.-W. Sun, Acc. Chem. Res. 2008, 41, 831-840;
- (2008) Acc. Chem. Res. , vol.41 , pp. 831-840
- Lin, G.-Q.¹ Xu, M.H.² Zhong, Y.-W.³ Sun, X.-W.⁴

37
- 63049135096
- g) F. Ferreira, C. Botuha, F. Chemla, A. Pérez-Luna, Chem. Soc. Rev. 2009, 38, 1162-1186.
- (2009) Chem. Soc. Rev. , vol.38 , pp. 1162-1186
- Ferreira, F.¹ Botuha, C.² Chemla, F.³ Pérez-Luna, A.⁴

38
- 0141628885
- a) D.J. Weix, J. A. Ellman, Org. Lett. 2003, 5, 1317-1320;
- (2003) Org. Lett. , vol.5 , pp. 1317-1320
- Weix, D.J.¹ Ellman, J.A.²

39
- 85026877407
- b) D. J. Weix, I A. Ellman, Org. Synth. 2005, 82, 157-165.
- (2005) Org. Synth. , vol.82 , pp. 157-165
- Weix, D.J.¹ Ellman, I.A.²

40
- 0033575410
- D. A. Cogan, G. Liu, J Ellman, Tetrahedron 1999, 55, 8883-8904.
- (1999) Tetrahedron , vol.55 , pp. 8883-8904
- Cogan, D.A.¹ Liu, G.² Ellman, J.³

41
- 64249103893
- a) M. Wakayama, J A. Ellman, J. Org. Chem. 2009, 74, 26462650;
- (2009) J. Org. Chem. , vol.74 , pp. 26462650
- Wakayama, M.¹ Ellman, J.A.²

42
- 65549159759
- b) V. K. Aggarwal, N. Barbero, E. M. McGarrigle, G. Mickle, R. Navas, J. R. Suárez, M. G. Unthank, M. Yar, Tetrahedron Lett. 2009, 50, 3482-3484.
- (2009) Tetrahedron Lett. , vol.50 , pp. 3482-3484
- Aggarwal, V.K.¹ Barbero, N.² McGarrigle, E.M.³ Mickle, G.⁴ Navas, R.⁵ Suárez, J.R.⁶ Unthank, M.G.⁷ Yar, M.⁸

43
- 0036558479
- For a review, see: J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669-1730.
- (2002) Chem. Rev. , vol.102 , pp. 1669-1730
- Scott, J.D.¹ Williams, R.M.²

44
- 0344899921
- For reviews, see: a) J. L. Vicario, D. Badia, L. Carrillo, I Etxebarria, Curr. Org. Chem. 2003, 7, 1775-1792;
- (2003) Curr. Org. Chem. , vol.7 , pp. 1775-1792
- Vicario, J.L.¹ Badia, D.² Carrillo, L.³ Etxebarria, I.⁴

45
- 5744254384
- b) A. B. J. Bracea, T. S. Kaufman, Tetrahedron 2004, 60, 10575-10610;
- (2004) Tetrahedron , vol.60 , pp. 10575-10610
- Bracea, A.B.J.¹ Kaufman, T.S.²

46
- 56549110286
- c) P. Siengalewicz, U. Rinner, I Mulzer, Chem. Soc. Rev. 2008, 37, 26762690.
- (2008) Chem. Soc. Rev. , vol.37 , pp. 26762690
- Siengalewicz, P.¹ Rinner, U.² Mulzer, I.³

47
- 60649106007
- For recent syntheses of substituted 2, 3, 4, 5-tetrahydro-l// benzazepines, see: a) I Crecente-Campo, M. P. Vázquez-Tato, J. A. Seijas, Tetrahedron 2009, 65, 2655-2659;
- (2009) Tetrahedron , vol.65 , pp. 2655-2659
- Crecente-Campo, I.¹ Vázquez-Tato, M.P.² Seijas, J.A.³

48
- 67649646687
- b) S. M. Husain, M. T. Heim, D. Schepmann, B. Wünsch, Tetrahedron: Asymmetry 2009, 20, 1383-1392.
- (2009) Tetrahedron: Asymmetry , vol.20 , pp. 1383-1392
- Husain, S.M.¹ Heim, M.T.² Schepmann, D.³ Wünsch, B.⁴

49
- 85040846778
- a) J. Weinstock, I P. Hieble, I W Wilson III, Drug Fut. 1985, 70, 645-697;
- (1985) Drug Fut. , vol.70 , pp. 645-697
- Weinstock, J.¹ Hieble, I.P.² Wilson III, I.W.³

50
- 0025326730
- b) I. Pettersson, T. Liljefors, K. Bogeso, J. Med. Chem. 1990, 33, 2197-2204;
- (1990) J. Med. Chem. , vol.33 , pp. 2197-2204
- Pettersson, I.¹ Liljefors, T.² Bogeso, K.³

51
- 13444252378
- c) W. L. Wu, D. A. Burnett, R. Spring, J. Med. Chem. 2005, 48, 680-693.
- (2005) J. Med. Chem. , vol.48 , pp. 680-693
- Wu, W.L.¹ Burnett, D.A.² Spring, R.³

52
- 0028951501
- K. K. Gnanalingham, A. J. Hunter, P. Jenner, C. D. Marsden, Psychopharmacology (Berlin, Ger.) 1995, 117, 403-412.
- (1995) Psychopharmacology (Berlin, Ger.) , vol.117 , pp. 403-412
- Gnanalingham, K.K.¹ Hunter, A.J.² Jenner, P.³ Marsden, C.D.⁴

53
- 34248562939
- A. D. Medhurst, A. R. Atkins, I. J Beresford, K. Brackenborough, M. A. Briggs, A. R. Calver, J. Cilia, J. E. Cluderay, B. Crook, I B. Davis, R. K. Davis, R. P. Davis, L. A. Dawson, A. G. Foley, I Gartlon, M. I. Gonzalez, T. Heslop, W. D. Hirst, C. Jennings, D. N. C. Jones, L. P. Lacroix, A. Martyn, S. Ociepka, A. Ray, C. M. Regan, J. C. Roberts, I Schogger, E. Southam, T. O. Stean, B. K. Trail, N. Upton, G. Wadsworth, I A. Wald, T. White, I Witherington, M. L. Woolley, A. Worby, D. M. Wilson, J. Pharmacol. Exp. Ther. 2007, 321, 1032-1045.
- (2007) J. Pharmacol. Exp. Ther. , vol.321 , pp. 1032-1045
- Medhurst, A.D.¹ Atkins, A.R.² Beresford, I.J.³ Brackenborough, K.⁴ Briggs, M.A.⁵ Calver, A.R.⁶ Cilia, J.⁷ Cluderay, J.E.⁸ Crook, B.⁹ Davis, I.B.¹⁰ Davis, R.K.¹¹ Davis, R.P.¹² Dawson, L.A.¹³ Foley, A.G.¹⁴ Gartlon, I.¹⁵ Gonzalez, M.I.¹⁶ Heslop, T.¹⁷ Hirst, W.D.¹⁸ Jennings, C.¹⁹ Jones, D.N.C.²⁰ more..

54
- 67649346112
- M. Medjahdi, J. C. González-Gómez, F. Foubelo, M. Yus, Heterocycles 2008, 76, 569-581.
- (2008) Heterocycles , vol.76 , pp. 569-581
- Medjahdi, M.¹ González-Gómez, J.C.² Foubelo, F.³ Yus, M.⁴

55
- 40849146803
- a) R. Almansa, D. Guijarro, M. Yus, Tetrahedron: Asymmetry 2008, 19, 603-606;
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 603-606
- Almansa, R.¹ Guijarro, D.² Yus, M.³

56
- 57049088500
- b) R. Almansa, D. Guijarro, M. Yus, Tetrahedron: Asymmetry 2008, 19, 2484-2491.
- (2008) Tetrahedron: Asymmetry , vol.19 , pp. 2484-2491
- Almansa, R.¹ Guijarro, D.² Yus, M.³

57
- 0036537789
- a) P. V. Bharatam, Amita, D. Kaur, J. Phys. Org. Chem. 2002, 15, 197-203;
- (2002) J. Phys. Org. Chem. , vol.15 , pp. 197-203
- Bharatam, P.V.¹ Kaur, A.D.²

58
- 0033993072
- b) F. V. Bharatam, P. Uppal, Amita, D. Kaur, J. Chem. Soc. Perkin Trans. 2 2000, 43-50.
- (2000) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 43-50
- Bharatam, F.V.¹ Uppal, P.² Kaur, A.D.³

59
- 0033756705
- F. Foubelo, C. Gómez, A. Gutiérrez, M. Yus, J. Heterocycl. Chem. 2000, 37, 1061-1064.
- (2000) J. Heterocycl. Chem. , vol.37 , pp. 1061-1064
- Foubelo, F.¹ Gómez, C.² Gutiérrez, A.³ Yus, M.⁴

60
- 0033582571
- G. Liu, D. A. Cogan, T. D. Owens, T. P. Tang, J. A. Ellman, J. Org. Chem. 1999, 64, 1278-1284.
- (1999) J. Org. Chem. , vol.64 , pp. 1278-1284
- Liu, G.¹ Cogan, D.A.² Owens, T.D.³ Tang, T.P.⁴ Ellman, J.A.⁵

61
- 0345799895
- SAINT, version 6.02A, Siemens Industrial Automation, Inc., Madison, WI
- SAINT, Area-Detector Integration Software, version 6.02A, Siemens Industrial Automation, Inc., Madison, WI, 1995.
- (1995) Area-Detector Integration Software

62
- 0003493382
- University of Göttingen, Göttingen
- G. M. Sheldrick, SADABS: Area-Detector Absorption Correction, University of Göttingen, Göttingen, 1996
- (1996) SADABS: Area-Detector Absorption Correction
- Sheldrick, G.M.¹

63
- 0004150157
- Programs for Crystal Structure Analysis (rel. 97-2), University of Göttingen, Göttingen
- G. M. Sheldrick, SHELX97 [includes SHELXS97, SHELXL97 and CIFTAB], Programs for Crystal Structure Analysis (rel. 97-2), University of Göttingen, Göttingen, 1998.
- (1998) SHELX97 [Includes SHELXS97, SHELXL97 and CIFTAB]
- Sheldrick, G.M.¹

64
- 11144256167
- D. Enders, V. Braig, M. Boudou, G. Raabe, Synthesis 2004, 2980-2990.
- (2004) Synthesis , pp. 2980-2990
- Enders, D.¹ Braig, V.² Boudou, M.³ Raabe, G.⁴

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