SCOPUS 정보 검색 플랫폼

Volumn 19, Issue 14, 2013, Pages 4614-4622

Preparation of stereodefined secondary alkyllithium compounds

(7) Seel, Stephanie a Dagousset, Guillaume a Thaler, Tobias a Frischmuth, Annette a Karaghiosoff, Konstantin a Zipse, Hendrik a Knochel, Paul a

a UNIVERSITY OF MUNICH (Germany)

Author keywords

diastereoselectivity; lithiation; solvent effects; substituent effects; synthetic methods

Indexed keywords

DIASTEREO-SELECTIVITY; LITHIATION; SOLVENT EFFECTS; SUBSTITUENT EFFECT; SYNTHETIC METHODS;

CHEMISTRY; SYNTHESIS (CHEMICAL);

OLIGOMERS;

IODINE; LITHIUM; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

IODINE; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; THERMODYNAMICS;

EID: 84875287687 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201204076 Document Type: Article

Times cited : (29)

References (78)

1
- 0003961355
- Elsevier, Philadelphia
- J. Clayden, Organolithiums: Selectivity for Synthesis, Elsevier, Philadelphia, 2002
- (2002) Organolithiums: Selectivity for Synthesis
- Clayden, J.¹

2
- 38749135630
- D. B. Collum, A. J. McNeil, A. Ramirez, Angew. Chem. 2007, 119, 3060-3077
- (2007) Angew. Chem. , vol.119 , pp. 3060-3077
- Collum, D.B.¹ McNeil, A.J.² Ramirez, A.³

3
- 34250883890
- Angew. Chem. Int. Ed. 2007, 46, 3002-3017
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3002-3017

4
- 15044354362
- M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004, 116, 2256-2276
- (2004) Angew. Chem. , vol.116 , pp. 2256-2276
- Whisler, M.C.¹ MacNeil, S.² Snieckus, V.³ Beak, P.⁴

5
- 3242659209
- Angew. Chem. Int. Ed. 2004, 43, 2206-2225.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2206-2225

6
- 0000232576
- A. Basu, S. Thayumanavan, Angew. Chem. 2002, 114, 740-763
- (2002) Angew. Chem. , vol.114 , pp. 740-763
- Basu, A.¹ Thayumanavan, S.²

7
- 0036495880
- Angew. Chem. Int. Ed. 2002, 41, 716-738
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 716-738

8
- 84922361901
- (Eds.: R. E. Gawley, J. S. Siegel), VHCA, Zürich, Wiley-VCH, Weinheim.
- Stereochemical aspects of Organolithium Compounds, Vol. 26 (Eds.:, R. E. Gawley, J. S. Siegel,), VHCA, Zürich, Wiley-VCH, Weinheim, 2010.
- (2010) Stereochemical Aspects of Organolithium Compounds, Vol. 26

9
- 0000854142
- D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410
- (1997) Angew. Chem. , vol.109 , pp. 2376-2410
- Hoppe, D.¹ Hense, T.²

10
- 0030694010
- Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2282-2316

11
- 63849186515
- D. Hoppe, Synthesis 2009, 43-55.
- (2009) Synthesis , pp. 43-55
- Hoppe, D.¹

12
- 61749088349
- W. K. Lee, Y. S. Park, P. Beak, Acc. Chem. Res. 2009, 42, 224-234.
- (2009) Acc. Chem. Res. , vol.42 , pp. 224-234
- Lee, W.K.¹ Park, Y.S.² Beak, P.³

13
- 0000898478
- T. Cohen, M.-T. Lin, J. Am. Chem. Soc. 1984, 106, 1130-1131
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1130-1131
- Cohen, T.¹ Lin, M.-T.²

14
- 0000588779
- W. C. Still, C. Sreekumar, J. Am. Chem. Soc. 1980, 102, 1201-1202
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 1201-1202
- Still, W.C.¹ Sreekumar, C.²

15
- 0001317003
- D. Hoppe, F. Hintze, P. Tebben, Angew. Chem. 1990, 102, 1455-1456
- (1990) Angew. Chem. , vol.102 , pp. 1455-1456
- Hoppe, D.¹ Hintze, F.² Tebben, P.³

16
- 79959948228
- F. M. Perna, A. Salomone, M. Dammacco, S. Florio, V. Capriati, Chem. Eur. J. 2011, 17, 8216-8225
- (2011) Chem. Eur. J. , vol.17 , pp. 8216-8225
- Perna, F.M.¹ Salomone, A.² Dammacco, M.³ Florio, S.⁴ Capriati, V.⁵

17
- 77955896059
- V. Capriati, S. Florio, F. M. Perna, A. Salomone, Chem. Eur. J. 2010, 16, 9778-9788
- (2010) Chem. Eur. J. , vol.16 , pp. 9778-9788
- Capriati, V.¹ Florio, S.² Perna, F.M.³ Salomone, A.⁴

18
- 2442515215
- V. Capriati, S. Florio, R. Luisi, I. Nuzzo, J. Org. Chem. 2004, 69, 3330-3335
- (2004) J. Org. Chem. , vol.69 , pp. 3330-3335
- Capriati, V.¹ Florio, S.² Luisi, R.³ Nuzzo, I.⁴

19
- 0006488934
- S. D. Rychnovsky, D. E. Mickus, Tetrahedron Lett. 1989, 30, 3011-3014
- (1989) Tetrahedron Lett. , vol.30 , pp. 3011-3014
- Rychnovsky, S.D.¹ Mickus, D.E.²

20
- 0032888368
- S. D. Rychnovsky, A. J. Buckmelter, V. H. Dahanukar, D. J. Skalitzky, J. Org. Chem. 1999, 64, 6849-6860
- (1999) J. Org. Chem. , vol.64 , pp. 6849-6860
- Rychnovsky, S.D.¹ Buckmelter, A.J.² Dahanukar, V.H.³ Skalitzky, D.J.⁴

21
- 36649015571
- D. C. Kapeller, L. Brecker, F. Hammerschmidt, Chem. Eur. J. 2007, 13, 9582-9588
- (2007) Chem. Eur. J. , vol.13 , pp. 9582-9588
- Kapeller, D.C.¹ Brecker, L.² Hammerschmidt, F.³

22
- 64149132146
- D. C. Kapeller, F. Hammerschmidt, J. Org. Chem. 2009, 74, 2380-2388
- (2009) J. Org. Chem. , vol.74 , pp. 2380-2388
- Kapeller, D.C.¹ Hammerschmidt, F.²

23
- 0000336059
- M. Schlosser, D. Limat, J. Am. Chem. Soc. 1995, 117, 12342-12343
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 12342-12343
- Schlosser, M.¹ Limat, D.²

24
- 34147175489
- R. Luisi, V. Capriati, S. Florio, B. Musio, Org. Lett. 2007, 9, 1263-1266
- (2007) Org. Lett. , vol.9 , pp. 1263-1266
- Luisi, R.¹ Capriati, V.² Florio, S.³ Musio, B.⁴

25
- 0033582569
- C. Serino, N. Stehle, Y. S. Park, S. Florio, P. Beak, J. Org. Chem. 1999, 64, 1160-1165
- (1999) J. Org. Chem. , vol.64 , pp. 1160-1165
- Serino, C.¹ Stehle, N.² Park, Y.S.³ Florio, S.⁴ Beak, P.⁵

26
- 0001423357
- R. E. Gawley, Q. Zhang, J. Am. Chem. Soc. 1993, 115, 7515-7516
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 7515-7516
- Gawley, R.E.¹ Zhang, Q.²

27
- 33747761620
- I. Coldham, S. Dufour, T. F. N. Haxell, J. J. Patel, G. Sanchez-Jimenez, J. Am. Chem. Soc. 2006, 128, 10943-10951
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 10943-10951
- Coldham, I.¹ Dufour, S.² Haxell, T.F.N.³ Patel, J.J.⁴ Sanchez-Jimenez, G.⁵

28
- 66249139590
- D. C. Kapeller, F. Hammerschmidt, Chem. Eur. J. 2009, 15, 5729-5739
- (2009) Chem. Eur. J. , vol.15 , pp. 5729-5739
- Kapeller, D.C.¹ Hammerschmidt, F.²

29
- 0000800334
- R. W. Hoffmann, R. K. Dress, T. Ruhland, A. Wenzel, Chem. Ber. 1995, 128, 861-870
- (1995) Chem. Ber. , vol.128 , pp. 861-870
- Hoffmann, R.W.¹ Dress, R.K.² Ruhland, T.³ Wenzel, A.⁴

30
- 77957302961
- J. J. Gammon, V. H. Gessner, G. R. Barker, J. Granander, A. C. Whitwood, C. Strohmann, P. O'Brien, B. Kelly, J. Am. Chem. Soc. 2010, 132, 13922-13927
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 13922-13927
- Gammon, J.J.¹ Gessner, V.H.² Barker, G.R.³ Granander, J.⁴ Whitwood, A.C.⁵ Strohmann, C.⁶ O'Brien, P.⁷ Kelly, B.⁸

31
- 77953878005
- V. H. Gessner, S. Dilsky, C. Strohmann, Chem. Commun. 2010, 46, 4719-4721
- (2010) Chem. Commun. , vol.46 , pp. 4719-4721
- Gessner, V.H.¹ Dilsky, S.² Strohmann, C.³

32
- 33748983227
- P. O′Brien, S. Warren, J. Chem. Soc. Perkin Trans. 1 1996, 2567-2573
- (1996) J. Chem. Soc. Perkin Trans. 1 , pp. 2567-2573
- Obrien, P.¹ Warren, S.²

33
- 37049069109
- R. W. Hoffmann, T. Ruhland, M. Bewersdorf, J. Chem. Soc. Chem. Commun. 1991, 195-196
- (1991) J. Chem. Soc. Chem. Commun. , pp. 195-196
- Hoffmann, R.W.¹ Ruhland, T.² Bewersdorf, M.³

34
- 39649090756
- D. C. Kapeller, F. Hammerschmidt, J. Am. Chem. Soc. 2008, 130, 2329-2335.
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 2329-2335
- Kapeller, D.C.¹ Hammerschmidt, F.²

35
- 84860794307
- J. Lefranc, A. M. Fournier, G. Mingat, S. Herbert, T. Marcelli, J. Clayden, J. Am. Chem. Soc. 2012, 134, 7286-7289
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 7286-7289
- Lefranc, J.¹ Fournier, A.M.² Mingat, G.³ Herbert, S.⁴ Marcelli, T.⁵ Clayden, J.⁶

36
- 0035915313
- J. Clayden, M. Helliwell, J. H. Pink, N. Westlund, J. Am. Chem. Soc. 2001, 123, 12449-12457
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 12449-12457
- Clayden, J.¹ Helliwell, M.² Pink, J.H.³ Westlund, N.⁴

37
- 84986676623
- R. W. Hoffmann, T. Rühl, F. Chemla, T. Zahneisen, Liebigs Ann. Chem. 1992, 719-724
- (1992) Liebigs Ann. Chem. , pp. 719-724
- Hoffmann, R.W.¹ Rühl, T.² Chemla, F.³ Zahneisen, T.⁴

38
- 0000600622
- P. R. Peoples, J. B. Grutzner, J. Am. Chem. Soc. 1980, 102, 4709-4715
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 4709-4715
- Peoples, P.R.¹ Grutzner, J.B.²

39
- 0032540964
- L. Prat, L. Mojovic, V. Levacher, G. Dupas, G. Quéguiner, J. Bourguignon, Tetrahedron: Asymmetry 1998, 9, 2509-2516.
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2509-2516
- Prat, L.¹ Mojovic, L.² Levacher, V.³ Dupas, G.⁴ Quéguiner, G.⁵ Bourguignon, J.⁶

40
- 0000688113
- I. Hoppe, M. Marsch, K. Harms, G. Boche, D. Hoppe, Angew. Chem. 1995, 107, 2328-2330
- (1995) Angew. Chem. , vol.107 , pp. 2328-2330
- Hoppe, I.¹ Marsch, M.² Harms, K.³ Boche, G.⁴ Hoppe, D.⁵

41
- 33748615119
- Angew. Chem. Int. Ed. Engl. 1995, 34, 2158-2160
- (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 2158-2160

42
- 0033617303
- M. D. Curtis, P. Beak, J. Org. Chem. 1999, 64, 2996-2997.
- (1999) J. Org. Chem. , vol.64 , pp. 2996-2997
- Curtis, M.D.¹ Beak, P.²

43
- 0001054481
- R. L. Letsinger, J. Am. Chem. Soc. 1950, 72, 4842
- (1950) J. Am. Chem. Soc. , vol.72 , pp. 4842
- Letsinger, R.L.¹

44
- 0001198464
- D. Y. Curtin, W. J., Jr. Koehl, J. Am. Chem. Soc. 1962, 84, 1967-1973.
- (1962) J. Am. Chem. Soc. , vol.84 , pp. 1967-1973
- Curtin, D.Y.¹ Koehl, W.J.Jr.²

45
- 84986835527
- H. J. Reich, M. A. Medina, M. D. Bowe, J. Am. Chem. Soc. 1992, 114, 11003-11004
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 11003-11004
- Reich, H.J.¹ Medina, M.A.² Bowe, M.D.³

46
- 0000898204
- W. H. Glaze, C. M. Selman, J. Org. Chem. 1968, 33, 1987-1990
- (1968) J. Org. Chem. , vol.33 , pp. 1987-1990
- Glaze, W.H.¹ Selman, C.M.²

47
- 0000256526
- W. H. Glaze, C. M. Selman, A. L. Ball, Jr., L. E. Bray, J. Org. Chem. 1969, 34, 641-644.
- (1969) J. Org. Chem. , vol.34 , pp. 641-644
- Glaze, W.H.¹ Selman, C.M.² Ball Jr., A.L.³ Bray, L.E.⁴

48
- 84982482243
- D. Seebach, H. Neumann, Chem. Ber. 1974, 107, 847-853
- (1974) Chem. Ber. , vol.107 , pp. 847-853
- Seebach, D.¹ Neumann, H.²

49
- 0001543586
- H. Neumann, D. Seebach, Tetrahedron Lett. 1976, 17, 4839-4842
- (1976) Tetrahedron Lett. , vol.17 , pp. 4839-4842
- Neumann, H.¹ Seebach, D.²

50
- 84942752381
- H. Neumann, D. Seebach, Chem. Ber. 1978, 111, 2785-2878
- (1978) Chem. Ber. , vol.111 , pp. 2785-2878
- Neumann, H.¹ Seebach, D.²

51
- 0002772829
- W. F. Bailey, J. J. Patricia, J. Organomet. Chem. 1988, 352, 1-46
- (1988) J. Organomet. Chem. , vol.352 , pp. 1-46
- Bailey, W.F.¹ Patricia, J.J.²

52
- 0001043464
- W. F. Bailey, E. R. Punzalan, J. Org. Chem. 1990, 55, 5404-5406
- (1990) J. Org. Chem. , vol.55 , pp. 5404-5406
- Bailey, W.F.¹ Punzalan, E.R.²

53
- 0001013027
- E.-I. Negishi, D. R. Swanson, C. J. Rousset, J. Org. Chem. 1990, 55, 5406-5409
- (1990) J. Org. Chem. , vol.55 , pp. 5406-5409
- Negishi, E.-I.¹ Swanson, D.R.² Rousset, C.J.³

54
- 33746458511
- W. F. Bailey, T. T. Nurmi, J. J. Patricia, W. Wang, J. Am. Chem. Soc. 1987, 109, 2442-2448
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 2442-2448
- Bailey, W.F.¹ Nurmi, T.T.² Patricia, J.J.³ Wang, W.⁴

55
- 0000690753
- E. C. Ashby, T. N. Pham, J. Org. Chem. 1987, 52, 1291-1300
- (1987) J. Org. Chem. , vol.52 , pp. 1291-1300
- Ashby, E.C.¹ Pham, T.N.²

56
- 0042388704
- W. F. Bailey, J. D. Brubaker, K. P. Jordan, J. Organomet. Chem. 2003, 681, 210-214.
- (2003) J. Organomet. Chem. , vol.681 , pp. 210-214
- Bailey, W.F.¹ Brubaker, J.D.² Jordan, K.P.³

57
- 33847218271
- A. Sakakura, A. Ukai, K. Ishihara, Nature 2007, 445, 900-903.
- (2007) Nature , vol.445 , pp. 900-903
- Sakakura, A.¹ Ukai, A.² Ishihara, K.³

58
- 68949147023
- G. L. Lange, C. Gottardo, Synth. Commun. 1990, 20, 1473-1479.
- (1990) Synth. Commun. , vol.20 , pp. 1473-1479
- Lange, G.L.¹ Gottardo, C.²

59
- 84891489831
- CCDC-890872 (β-(eq)-15 a), CCDC-890873 (cis -(ax)-1), CCDC-890874 (neomen-(ax)-11 b), and CCDC-890875 (trans -(eq)-5 f) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.

60
- 33845378731
- H. J. Reich, N. H. Phillips, I. L. Reich, J. Am. Chem. Soc. 1985, 107, 4101-4103
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 4101-4103
- Reich, H.J.¹ Phillips, N.H.² Reich, I.L.³

61
- 0001488536
- D. Hoppe, A. Carstens, T. Krämer, Angew. Chem. 1990, 102, 1457-1459
- (1990) Angew. Chem. , vol.102 , pp. 1457-1459
- Hoppe, D.¹ Carstens, A.² Krämer, T.³

62
- 0343177680
- Angew. Chem. Int. Ed. Engl. 1990, 29, 1424-1425
- (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 1424-1425

63
- 0030863813
- F. Hammerschmidt, A. Hanninger, H. Völlenkle, Chem. Eur. J. 1997, 3, 1728-1732
- (1997) Chem. Eur. J. , vol.3 , pp. 1728-1732
- Hammerschmidt, F.¹ Hanninger, A.² Völlenkle, H.³

64
- 84856918166
- C. Unkelbach, B. C. Abele, K. Lehmen, D. Schildbach, B. Waerder, K. Wild, C. Strohmann, Chem. Commun. 2012, 48, 2492-2494.
- (2012) Chem. Commun. , vol.48 , pp. 2492-2494
- Unkelbach, C.¹ Abele, B.C.² Lehmen, K.³ Schildbach, D.⁴ Waerder, B.⁵ Wild, K.⁶ Strohmann, C.⁷

65
- 70349125054
- T. S. De Vries, A. Goswami, L. R. Liou, J. M. Gruver, E. Jayne, D. B. Collum, J. Am. Chem. Soc. 2009, 131, 13142-13154
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 13142-13154
- De Vries, T.S.¹ Goswami, A.² Liou, L.R.³ Gruver, J.M.⁴ Jayne, E.⁵ Collum, D.B.⁶

66
- 0007004440
- S. Gronert, A., Jr. Streitwieser, J. Am. Chem. Soc. 1986, 108, 7016-7022
- (1986) J. Am. Chem. Soc. , vol.108 , pp. 7016-7022
- Gronert, S.¹ Streitwieser, A.Jr.²

67
- 78049368868
- G. Carbone, P. O'Brien, G. Hilmersson, J. Am. Chem. Soc. 2010, 132, 15445-15450
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15445-15450
- Carbone, G.¹ O'Brien, P.² Hilmersson, G.³

68
- 0000254037
- H. J. Reich, J. P. Borst, J. Am. Chem. Soc. 1991, 113, 1835-1837.
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 1835-1837
- Reich, H.J.¹ Borst, J.P.²

69
- 58849153700
- K. J. Singh, A. C. Hoepker, D. B. Collum, J. Am. Chem. Soc. 2008, 130, 18008-18017
- (2008) J. Am. Chem. Soc. , vol.130 , pp. 18008-18017
- Singh, K.J.¹ Hoepker, A.C.² Collum, D.B.³

70
- 78149269548
- Y. Ma, A. C. Hoepker, L. Gupta, M. F. Faggin, D. B. Collum, J. Am. Chem. Soc. 2010, 132, 15610-15623
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 15610-15623
- Ma, Y.¹ Hoepker, A.C.² Gupta, L.³ Faggin, M.F.⁴ Collum, D.B.⁵

71
- 79955688674
- A. C. Hoepker, L. Gupta, Y. Ma, M. F. Faggin, D. B. Collum, J. Am. Chem. Soc. 2011, 133, 7135-7151
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 7135-7151
- Hoepker, A.C.¹ Gupta, L.² Ma, Y.³ Faggin, M.F.⁴ Collum, D.B.⁵

72
- 4644364362
- L. M. Pratt, Mini-Rev. Org. Chem. 2004, 1, 209-217.
- (2004) Mini-Rev. Org. Chem. , vol.1 , pp. 209-217
- Pratt, L.M.¹

73
- 0035250099
- O. Kwon, F. Sevin, M. L. McKee, J. Phys. Chem. A 2001, 105, 913-922
- (2001) J. Phys. Chem. A , vol.105 , pp. 913-922
- Kwon, O.¹ Sevin, F.² McKee, M.L.³

74
- 0035956474
- F. Hæffner, T. Brinck, Organometallics 2001, 20, 5134-5138
- (2001) Organometallics , vol.20 , pp. 5134-5138
- Hæffner, F.¹ Brinck, T.²

75
- 33644640406
- K. Ando, J. Org. Chem. 2006, 71, 1837-1850.
- (2006) J. Org. Chem. , vol.71 , pp. 1837-1850
- Ando, K.¹

76
- 0001097026
- T. Kottke, D. Stalke, Angew. Chem. 1993, 105, 619-621
- (1993) Angew. Chem. , vol.105 , pp. 619-621
- Kottke, T.¹ Stalke, D.²

77
- 33748226760
- Angew. Chem. Int. Ed. Engl. 1993, 32, 580-582.
- (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 580-582

78
- 0001148137
- R. Zerger, W. Rhine, G. Stucky, J. Am. Chem. Soc. 1974, 96, 6048-6055.
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 6048-6055
- Zerger, R.¹ Rhine, W.² Stucky, G.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.