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Volumn 2009, Issue 14, 2009, Pages 266-300

Variation in sites of lithiation of substituted n-benzylpivalamides and N'-benzyl-N,N-dimethylureas: Application in synthesis

(5) Smith, Keith a El Hiti, Gamal A a Hegazy, Amany S a Fekri, Ahmed a Kariuki, Benson M a

a CARDIFF UNIVERSITY (United Kingdom)

Author keywords

Directed ortho lithiation; Electrophilic substitution; Side chain lithiation; Substituted benzylamines; Synthesis

Indexed keywords

EID: 77953190459 PISSN: 1551-7012 EISSN: 15517004 Source Type: Journal
DOI: 10.3998/ark.5550190.0010.e24 Document Type: Article

Times cited : (15)

References (71)

1
- 0003961355
- See, for example: a, Pergamon: Oxford
- See, for example: (a) Clayden, J. Organolithiums: Selectivity for Synthesis, Pergamon: Oxford, 2002.
- (2002) Organolithiums: Selectivity for Synthesis
- Clayden, J.¹

2
- 0004219714
- 2nd ed.; Wiley: Chichester
- (b) Schlosser, M. Organometallics in Synthesis, 2nd ed.; Wiley: Chichester, 2002; pp 1-352.
- (2002) Organometallics in Synthesis , pp. 1-352
- Schlosser, M.¹

3
- 0001577546
- See, for example: a
- See, for example: (a) Gschwend, H. W.; Hamdan, A. J. Org. Chem. 1975, 40, 2008.
- (1975) J. Org. Chem. , vol.40 , pp. 2008
- Gschwend, H.W.¹ Hamdan, A.²

4
- 0000119297
- (b) Fitt, J. J.; Gschwend, H. W. J. Org. Chem. 1976, 41, 4029.
- (1976) J. Org. Chem. , vol.41 , pp. 4029
- Fitt, J.J.¹ Gschwend, H.W.²

5
- 33845560452
- (c) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133.
- (1979) J. Org. Chem. , vol.44 , pp. 1133
- Fuhrer, W.¹ Gschwend, H.W.²

6
- 33845555248
- (d) Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306.
- (1982) Acc. Chem. Res. , vol.15 , pp. 306
- Beak, P.¹ Snieckus, V.²

7
- 0242352416
- (e) Nájera, C.; Sansano, J. M.; Yus, M. Tetrahedron 2003, 59, 9255.
- (2003) Tetrahedron. , vol.59 , pp. 9255
- Nájera, C.¹ Sansano, J.M.² Yus, M.³

8
- 3242659209
- (f) Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. Int. Ed. 2004, 43, 2206.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2206
- Whisler, M.C.¹ MacNeil, S.² Snieckus, V.³ Beak, P.⁴

9
- 33847612747
- (g) Chadwick, S. T.; Ramirez, A.; Gupta, L.; Collum, D. B. J. Am. Chem. Soc. 2007, 129, 2259.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 2259
- Chadwick, S.T.¹ Ramirez, A.² Gupta, L.³ Collum, D.B.⁴

10
- 33845469631
- See, for example: a
- See, for example: (a) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471.
- (1984) Chem. Rev. , vol.84 , pp. 471
- Beak, P.¹ Zajdel, W.J.² Reitz, D.B.³

11
- 0012397313
- (b) Snieckus, V. Chem. Rev. 1990, 90, 879.
- (1990) Chem. Rev. , vol.90 , pp. 879
- Snieckus, V.¹

12
- 0034254145
- (c) El-Hiti, G. A. Heterocycles 2000, 53, 1839.
- (2000) Heterocycles , vol.53 , pp. 1839
- El-Hiti, G.A.¹

13
- 0035821359
- (d) Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4059.
- (2001) Tetrahedron. , vol.57 , pp. 4059
- Mongin, F.¹ Quéguiner, G.²

14
- 0035927228
- (e) Turck, A.; Plé, N.; Mongin, F.; Quéguiner, G. Tetrahedron 2001, 57, 4489.
- (2001) Tetrahedron. , vol.57 , pp. 4489
- Turck, A.¹ Plé, N.² Mongin, F.³ Quéguiner, G.⁴

15
- 0036643421
- (f) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150.
- (2002) J. Organomet. Chem. , vol.653 , pp. 150
- Anctil, E.J.-G.¹ Snieckus, V.²

16
- 9144251649
- (g) Smith, K.; El-Hiti, G. A. Curr. Org. Synth. 2004, 1, 253.
- (2004) Curr. Org. Synth , vol.1 , pp. 253
- Smith, K.¹ El-Hiti, G.A.²

17
- 2942530950
- (h) Chinchilla, R.; Nájera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
- (2004) Chem. Rev. , vol.104 , pp. 2667
- Chinchilla, R.¹ Nájera, C.² Yus, M.³

18
- 12344258124
- (i) Schlosser, M. Angew. Chem. Int. Ed. 2005, 44, 376.
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 376
- Schlosser, M.¹

19
- 14844288305
- (j) Foubelo, F.; Yus, M. Curr. Org. Chem. 2005, 9, 459.
- (2005) Curr. Org. Chem. , vol.9 , pp. 459
- Foubelo, F.¹ Yus, M.²

20
- 65949094337
- (k) Rathman, T. L.; Bailey, W. F. Org. Process Res. Dev. 2009, 13, 144.
- (2009) Org. Process Res. Dev. , vol.13 , pp. 144
- Rathman, T.L.¹ Bailey, W.F.²

21
- 9444281977
- (l) Florio, S.; Aggarwal, V.; Salomone, A. Org. Lett. 2004, 6, 4191.
- (2004) Org. Lett. , vol.6 , pp. 4191
- Florio, S.¹ Aggarwal, V.² Salomone, A.³

22
- 47249116632
- (m) Capriati, V.; Florio, S.; Luisi, R. Chem. Rev. 2008, 108, 1918.
- (2008) Chem. Rev. , vol.108 , pp. 1918
- Capriati, V.¹ Florio, S.² Luisi, R.³

23
- 77955903246
- (n) Florio, S.; Capriati, V.; Salomone, A. Topics in Stereochemistry. 2010, 26, 135.
- (2010) Topics in Stereochemistry , vol.26 , pp. 135
- Florio, S.¹ Capriati, V.² Salomone, A.³

24
- 23044453131
- Recent examples for substituted benzenes: a
- Recent examples for substituted benzenes: (a) Clayden, J.; Turner, H.; Pickworth, M.; Adler, T. Org. Lett. 2005, 7, 3147.
- (2005) Org. Lett. , vol.7 , pp. 3147
- Clayden, J.¹ Turner, H.² Pickworth, M.³ Adler, T.⁴

25
- 14644411778
- (b) Chodakowski, J.; Kliś, T.; Serwatowski, J. Tetrahedron Lett. 2005, 46, 1963.
- (2005) Tetrahedron. Lett. , vol.46 , pp. 1963
- Chodakowski, J.¹ Kliś, T.² Serwatowski, J.³

26
- 33747769010
- (c) Clayden, J.; Dufour, J. Tetrahedron Lett. 2006, 47, 6945.
- (2006) Tetrahedron. Lett. , vol.47 , pp. 6945
- Clayden, J.¹ Dufour, J.²

27
- 39749183989
- (d) Burgos, P. O.; Fernández, I.; Iglesias, M. J.; García-Granda, S.; Ortiz, F. L. Org. Lett. 2008, 10, 537.
- (2008) Org. Lett. , vol.10 , pp. 537
- Burgos, P.O.¹ Fernández, I.² Iglesias, M.J.³ García-Granda, S.⁴ Ortiz, F.L.⁵

28
- 44349183652
- (e) Wilkinson, J. A.; Raiber, E.-A.; Ducki, S. Tetrahedron 2008, 64, 6329.
- (2008) Tetrahedron. , vol.64 , pp. 6329
- Wilkinson, J.A.¹ Raiber, E.-A.² Ducki, S.³

29
- 37249059015
- (f) Porcs-Makkay, M.; Komáromi, A.; Lukács, G.; Simig, G. Tetrahedron 2008, 64, 1029.
- (2008) Tetrahedron. , vol.64 , pp. 1029
- Porcs-Makkay, M.¹ Komáromi, A.² Lukács, G.³ Simig, G.⁴

30
- 39649119396
- (g) Castanet, A.-S.; Tilly, D.; Véron, J.-B.; Samanta, S. S.; De, A.; Ganguly, T.; Mortier, J. Tetrahedron 2008, 64, 3331.
- (2008) Tetrahedron. , vol.64 , pp. 3331
- Castanet, A.-S.¹ Tilly, D.² Véron, J.-B.³ Samanta, S.S.⁴ De, A.⁵ Ganguly, T.⁶ Mortier, J.⁷

31
- 57649108146
- (h) Michon, C.; Murai, M.; Nakatsu, M.; Uenishi, J.; Uemura M. Tetrahedron 2009, 65, 752.
- (2009) Tetrahedron. , vol.65 , pp. 752
- Michon, C.¹ Murai, M.² Nakatsu, M.³ Uenishi, J.⁴ Uemura, M.⁵

32
- 33747407346
- Recent examples for substituted heterocycles: a
- Recent examples for substituted heterocycles: (a) Philipova, I.; Dobrikov, G.; Krumova, K.; Kaneti, J. J. Heterocycl. Chem. 2006, 43, 1057.
- (2006) J. Heterocycl. Chem. , vol.43 , pp. 1057
- Philipova, I.¹ Dobrikov, G.² Krumova, K.³ Kaneti, J.⁴

33
- 33846146669
- (b) Robert, N.; Bonneau, A.-L.; Hoarau, C.; Marsais, F. Org. Lett. 2006, 8, 6071.
- (2006) Org. Lett. , vol.8 , pp. 6071
- Robert, N.¹ Bonneau, A.-L.² Hoarau, C.³ Marsais, F.⁴

34
- 33746653639
- (c) Aliyenne, A. O.; Khiari, J. E.; Kraïem, J.; Kacem, Y.; Hassine, B. B. Tetrahedron Lett. 2006, 47, 6405.
- (2006) Tetrahedron. Lett. , vol.47 , pp. 6405
- Aliyenne, A.O.¹ Khiari, J.E.² Kraïem, J.³ Kacem, Y.⁴ Hassine, B.B.⁵

35
- 33646581653
- (d) Comoy, C.; Banaszak, E.; Fort, Y. Tetrahedron 2006, 62, 6036.
- (2006) Tetrahedron. , vol.62 , pp. 6036
- Comoy, C.¹ Banaszak, E.² Fort, Y.³

36
- 34147175489
- (e) Luisi, R.; Capriati, V.; Florio, S.; Musio, B. Org. Lett. 2007, 9, 1263.
- (2007) Org. Lett. , vol.9 , pp. 1263
- Luisi, R.¹ Capriati, V.² Florio, S.³ Musio, B.⁴

37
- 54049130906
- (f) Clayden, J.; Hennecke, U. Org. Lett. 2008, 10, 3567.
- (2008) Org. Lett. , vol.10 , pp. 3567
- Clayden, J.¹ Hennecke, U.²

38
- 44949111442
- (g) McLaughlin, M.; Marcantonio, K.; Chen, C.; Davies, I. W. J. Org. Chem. 2008, 73, 4309.
- (2008) J. Org. Chem. , vol.73 , pp. 4309
- McLaughlin, M.¹ Marcantonio, K.² Chen, C.³ Davies, I.W.⁴

39
- 42149123402
- (h) Capriati, V.; Florio, S.; Luisi, R.; Mazzanti, A.; Musio, B. J. Org. Chem. 2008, 73, 3197.
- (2008) J. Org. Chem. , vol.73 , pp. 3197
- Capriati, V.¹ Florio, S.² Luisi, R.³ Mazzanti, A.⁴ Musio, B.⁵

40
- 57449089362
- (i) Affortunato, F.; Florio, S.; Luisi, R.; Musio B. J. Org. Chem. 2008, 73, 9214.
- (2008) J. Org. Chem. , vol.73 , pp. 9214
- Affortunato, F.¹ Florio, S.² Luisi, R.³ Musio, B.⁴

41
- 37049073944
- See, for example: a
- See, for example: (a) Smith, K.; El-Hiti, G. A.; Abdo, M. A.; Abdel-Megeed, M. F. J. Chem. Soc., Perkin Trans. 1 1995, 1029.
- (1995) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1029
- Smith, K.¹ El-Hiti, G.A.² Abdo, M.A.³ Abdel-Megeed, M.F.⁴

42
- 0030064335
- (b) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 647.
- (1996) J. Org. Chem. , vol.61 , pp. 647
- Smith, K.¹ El-Hiti, G.A.² Abdel-Megeed, M.F.³ Abdo, M.A.⁴

43
- 0030060065
- (c) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F.; Abdo, M. A. J. Org. Chem. 1996, 61, 656.
- (1996) J. Org. Chem. , vol.61 , pp. 656
- Smith, K.¹ El-Hiti, G.A.² Abdel-Megeed, M.F.³ Abdo, M.A.⁴

44
- 0002421134
- (d) Smith, K.; El-Hiti, G. A.; Pritchard, G. J.; Hamilton, A. J. Chem. Soc., Perkin Trans. 1 1999, 2299.
- (1999) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2299
- Smith, K.¹ El-Hiti, G.A.² Pritchard, G.J.³ Hamilton, A.⁴

45
- 0000647572
- (e) Smith, K.; El-Hiti, G. A.; Shukla, A. P. J. Chem. Soc., Perkin Trans. 1 1999, 2305.
- (1999) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2305
- Smith, K.¹ El-Hiti, G.A.² Shukla, A.P.³

46
- 0141730251
- (f) Smith, K.; El-Hiti, G. A.; Hawes, A. C. Synthesis 2003, 2047.
- (2003) Synthesis , pp. 2047
- Smith, K.¹ El-Hiti, G.A.² Hawes, A.C.³

47
- 0242656264
- (g) Smith, K.; El-Hiti, G. A.; Mahgoub, S. A. Synthesis 2003, 2345.
- (2003) Synthesis , pp. 2345
- Smith, K.¹ El-Hiti, G.A.² Mahgoub, S.A.³

48
- 0347950984
- (h) El-Hiti, G. A. Synthesis 2003, 2799.
- (2003) Synthesis , pp. 2799
- El-Hiti, G.A.¹

49
- 4544333635
- (i) Smith, K.; El-Hiti, G. A.; Abdel-Megeed, M. F. Synthesis 2004, 2121.
- (2004) Synthesis , pp. 2121
- Smith, K.¹ El-Hiti, G.A.² Abdel-Megeed, M.F.³

50
- 1442311007
- (j) El-Hiti, G. A. Synthesis 2004, 363.
- (2004) Synthesis , pp. 363
- El-Hiti, G.A.¹

51
- 27944457751
- (k) Smith, K.; El-Hiti, G. A.; Hegazy, A. S. J. Sulfur Chem. 2005, 26, 121.
- (2005) J. Sulfur Chem. , vol.26 , pp. 121
- Smith, K.¹ El-Hiti, G.A.² Hegazy, A.S.³

52
- 27944499777
- (l) Smith, K.; El-Hiti, G. A.; Hegazy, A. S. Synthesis 2005, 2951.
- (2005) Synthesis , pp. 2951
- Smith, K.¹ El-Hiti, G.A.² Hegazy, A.S.³

53
- 33846930368
- (m) Smith, K.; Barratt, M. L. J. Org. Chem. 2007, 72, 1031.
- (2007) J. Org. Chem. , vol.72 , pp. 1031
- Smith, K.¹ Barratt, M.L.²

54
- 0027527645
- Katsoulos, K.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263.
- (1993) Tetrahedron. Lett. , vol.34 , pp. 6263
- Katsoulos, K.¹ Schlosser, M.²

55
- 0043020915
- Simig, G.; Schlosser, M. Tetrahedron Lett. 1988, 29, 4277.
- (1988) Tetrahedron. Lett. , vol.29 , pp. 4277
- Simig, G.¹ Schlosser, M.²

56
- 69249120921
- Smith, K.; El-Hiti, G. A.; Hegazy, A. S. Synlett 2009, 2242.
- (2009) Synlett , pp. 2242
- Smith, K.¹ El-Hiti, G.A.² Hegazy, A.S.³

57
- 85069278939
- PhD Thesis, Cardiff University: Cardiff, UK
- Hegazy, A. S. Directed Lithiation of Substituted Benzylamines, PhD Thesis, Cardiff University: Cardiff, UK, 2009.
- (2009) Directed Lithiation of Substituted Benzylamines
- Hegazy, A.S.¹

58
- 0000813255
- (a) Gilman, H.; Gaj, B. J. J. Org. Chem. 1957, 22, 1165.
- (1957) J. Org. Chem. , vol.22 , pp. 1165
- Gilman, H.¹ Gaj, B.J.²

59
- 0001779969
- (b) Honeycutt, S. J. Organomet. Chem. 1971, 29, 1.
- (1971) J. Organomet. Chem. , vol.29 , pp. 1
- Honeycutt, S.¹

60
- 0001043536
- (c) Bates, R. E.; Kroposki, L. M.; Potter, D. E. J. Org. Chem. 1972, 37, 560.
- (1972) J. Org. Chem. , vol.37 , pp. 560
- Bates, R.E.¹ Kroposki, L.M.² Potter, D.E.³

61
- 0001469577
- (d) Jung, M. E.; Blum, R. B. Tetrahedron Lett. 1977, 18, 3791.
- (1977) Tetrahedron. Lett. , vol.18 , pp. 3791
- Jung, M.E.¹ Blum, R.B.²

62
- 84943920736
- Sheldrick, G. M. Acta Crystallogr., Sect. A. 1990, 46, 467.
- (1990) Acta Crystallogr., Sect. A , vol.46 , pp. 467
- Sheldrick, G.M.¹

63
- 0004150157
- Universität Göttingen
- Sheldrick, G. M. SHELXS-97, Program for Crystal Structure Refinement, Universität Göttingen, 1997.
- (1997) SHELXS-97, Program for Crystal Structure Refinement
- Sheldrick, G.M.¹

64
- 0344743411
- Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
- (1967) J. Organomet. Chem. , vol.9 , pp. 165
- Watson, S.C.¹ Eastham, J.F.²

65
- 0003905534
- 5th ed.; Longman: Harlow
- (a) Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: Harlow, 1989.
- (1989) Vogel's Textbook of Practical Organic Chemistry

66
- 0004055425
- 3rd ed.; Pergamon: Oxford
- (b) Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.
- (1988) Purification of Laboratory Chemicals
- Perrin, D.D.¹ Armarego, W.L.F.²

67
- 85018374598
- Martínez, A. G.; Alvarez, R. M.; Vilar, E. T.; Fraile, A. G.; Hanack, M.; Subramanian, L. R. Tetraderron Lett. 1989, 30, 581.
- (1989) Tetraderron Lett. , vol.30 , pp. 581
- Martínez, A.G.¹ Alvarez, R.M.² Vilar, E.T.³ Fraile, A.G.⁴ Hanack, M.⁵ Subramanian, L.R.⁶

68
- 0035958499
- (a) Darbeau, R. W.; Pease, R. S.; Gibble, R. E. J. Org. Chem. 2001, 66, 5027.
- (2001) J. Org. Chem. , vol.66 , pp. 5027
- Darbeau, R.W.¹ Pease, R.S.² Gibble, R.E.³

69
- 0037012822
- (b) Darbeau, R. W.; Pease, R. S.; Perez, E. V. J. Org. Chem. 2002, 67, 2942.
- (2002) J. Org. Chem. , vol.67 , pp. 2942
- Darbeau, R.W.¹ Pease, R.S.² Perez, E.V.³

70
- 0000927390
- Anastassiou, A. G.; Hammer, R. B. J. Am. Chem. Soc. 1972, 94, 303.
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 303
- Anastassiou, A.G.¹ Hammer, R.B.²

71
- 0017699605
- Borgna, P.; Vicarini, L.; Calderara, G. Farmaco [Sci.] 1977, 32, 813.
- (1977) Farmaco [Sci.] , vol.32 , pp. 813
- Borgna, P.¹ Vicarini, L.² Calderara, G.³

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