SCOPUS 정보 검색 플랫폼

Volumn , Issue 19, 2007, Pages 3179-3190

Enantioselective γ-deprotonation of alkyl-substituted O-1,3-butadien-2-yl carbamates and regioselective asymmetric homoaldol reaction

(4) Chedid, Roland Bou a Fröhlich, Roland a Wibbeling, Birgit a Hoppe, Dieter a

a UNIVERSITY OF MÜNSTER (Germany)

Author keywords

( ) Sparteine; Asymmetric synthesis; Carbanions; Cross coupling; Homoaldol reaction

Indexed keywords

EID: 34447304399 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.200700131 Document Type: Article

Times cited : (8)

References (56)

1
- 33746592076
- D. Hoppe, R. Bou Chedid, R. Fröhlich, Org. Lett. 2006, 8, 3061.
- (2006) Org. Lett , vol.8 , pp. 3061
- Hoppe, D.¹ Bou Chedid, R.² Fröhlich, R.³

2
- 34447320668
- D. Hoppe, R. Bou Chedid, M. Brümmer, R. Fröhlich, B. Wibbeling, Angew. Chem. 2007, 119, 3192;
- (2007) Angew. Chem , vol.119 , pp. 3192
- Hoppe, D.¹ Bou Chedid, R.² Brümmer, M.³ Fröhlich, R.⁴ Wibbeling, B.⁵

3
- 34250866214
- Angew. Chem. Int. Ed. 2007, 46, 3131.
- (2007) Chem. Int. Ed , vol.46 , pp. 3131
- Angew¹

4
- 0001854238
- D. Hoppe, O. Zschage, Angew. Chem. 1989, 101, 67;
- (1989) Angew. Chem , vol.101 , pp. 67
- Hoppe, D.¹ Zschage, O.²

5
- 0003176096
- Angew. Chem. Int. Ed. Engl. 1989, 28, 69.
- (1989) Angew. Chem. Int. Ed. Engl , vol.28 , pp. 69

6
- 0000854142
- Reviews: a
- Reviews: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376;
- (1997) Angew. Chem , vol.109 , pp. 2376
- Hoppe, D.¹ Hense, T.²

7
- 0030694010
- Angew. Chem. Int. Ed. Engl. 1997, 36, 2282;
- (1997) Angew. Chem. Int. Ed. Engl , vol.36 , pp. 2282

8
- 34447345875
- D. Hoppe, F. Marr, M. Brüggemann, in Organolithiums in Enantioselective Synthesis (Ed.: D. M. Hodgson); Topics in Organometallic Chemistry; Springer-Verlag: Berlin, 2003; 5, p. 61;
- b) D. Hoppe, F. Marr, M. Brüggemann, in Organolithiums in Enantioselective Synthesis (Ed.: D. M. Hodgson); Topics in Organometallic Chemistry; Springer-Verlag: Berlin, 2003; vol. 5, p. 61;

9
- 34447295014
- P. Beak, T. A. Johnson, D. D. Kim, S. H. Lim, in Organolithiums in Enantioselective Synthesis (Ed.: D. M. Hodgson); Topics in Organometallic Chemistry; Springer-Verlag: Berlin, 2003; 5, p. 134;
- c) P. Beak, T. A. Johnson, D. D. Kim, S. H. Lim, in Organolithiums in Enantioselective Synthesis (Ed.: D. M. Hodgson); Topics in Organometallic Chemistry; Springer-Verlag: Berlin, 2003; vol. 5, p. 134;

10
- 18844423506
- Eds, Z. Rappoport, I. Marek, John Wiley & Sons Ltd, Chichester, UK
- d) D. Hoppe, G. Christoph, in Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I. Marek); John Wiley & Sons Ltd, Chichester, UK, 2004; vol. 2, p. 1055;
- (2004) Chemistry of Organolithium Compounds , vol.2 , pp. 1055
- Hoppe, D.¹ Christoph, G.²

11
- 0033020763
- e) H. Ahlbrecht, U. Beyer, Synthesis 1999, 365.
- (1999) Synthesis , pp. 365
- Ahlbrecht, H.¹ Beyer, U.²

12
- 0000163012
- a) D. Hoppe, Angew. Chem. 1984, 96, 930;
- (1984) Angew. Chem , vol.96 , pp. 930
- Hoppe, D.¹

13
- 0006896915
- Angew. Chem. Int. Ed. Engl. 1984, 23, 931;
- (1984) Angew. Chem. Int. Ed. Engl , vol.23 , pp. 931

14
- 34447319831
- 4th ed, Eds, G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Thieme: Stuttgart, New York
- b) D. Hoppe, in Methoden der Org. Chem., 4th ed. (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann); Thieme: Stuttgart, New York, 1995; vol. 21b.
- (1995) Methoden der Org. Chem , vol.21 b
- Hoppe, D.¹

15
- 24144492430
- 2nd ed, A. de Meijere, F. Diedrich, Eds, VCH: Weinheim
- a) E. Negishi, X. Zeng, Z. Tan, M. Qian, Q. Hu, Z. Huang, in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; A. de Meijere, F. Diedrich, Eds.; VCH: Weinheim, 2004; vol. 2, p. 815;
- (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.2 , pp. 815
- Negishi, E.¹ Zeng, X.² Tan, Z.³ Qian, M.⁴ Hu, Q.⁵ Huang, Z.⁶

16
- 0038032208
- Ed, E. Negishi, John Wiley & Sons Inc
- b) A. Suzuki, Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: E. Negishi.); John Wiley & Sons Inc. 2002, vol. 1, p. 249.
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 249
- Suzuki, A.¹

17
- 0003780608
- Reviews: a, 1st ed, Springer-Verlag: Berlin
- Reviews: a) M. T. Reetz, Organotitanium Reagents in Organic Synthesis, 1st ed.; Springer-Verlag: Berlin, 1986;
- (1986) Organotitanium Reagents in Organic Synthesis
- Reetz, M.T.¹

18
- 0002291128
- b) B. Weidmann, D. Seebach, Angew. Chem. 1983, 95, 12;
- (1983) Angew. Chem , vol.95 , pp. 12
- Weidmann, B.¹ Seebach, D.²

19
- 1642336240
- Angew. Chem. Int. Ed. Engl. 1983, 22, 32;
- (1983) Angew. Chem. Int. Ed. Engl , vol.22 , pp. 32

20
- 0242632891
- Organotitanium Chemistry
- 2nd ed, Schlosser, M, Ed, Wiley: Chichester
- c) M. T. Reetz, Organotitanium Chemistry, in Organometallics in Synthesis, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, 2002; p. 817.
- (2002) Organometallics in Synthesis , pp. 817
- Reetz, M.T.¹

21
- 0000898481
- a) D. Hoppe, R. Hanko, A. Brönneke, F. Lichtenberg, E. van Hülsen, Chem. Ber. 1985, 118, 2822;
- (1985) Chem. Ber , vol.118 , pp. 2822
- Hoppe, D.¹ Hanko, R.² Brönneke, A.³ Lichtenberg, F.⁴ van Hülsen, E.⁵

22
- 33746608701
- b) D. Hoppe, K. Behrens, R. Fröhlich, O. Meyer, Eur. J. Org. Chem. 1998, 2397.
- (1998) Eur. J. Org. Chem , pp. 2397
- Hoppe, D.¹ Behrens, K.² Fröhlich, R.³ Meyer, O.⁴

23
- 33646245445
- a) X. J. Wang, Y. Li, C. X. Zhang, J. Chin. Chem. Soc. 2003, 50, 1183;
- (2003) J. Chin. Chem. Soc , vol.50 , pp. 1183
- Wang, X.J.¹ Li, Y.² Zhang, C.X.³

24
- 0028207394
- b) A. K. Ghosh, H. Y. Lee, W. J. Thompson, C. Culberson, M. K. Holloway, S. P. McKee, P. M. Munson, T. T. Duong, A. M. Smith, P. L. Darke, J. A. Zugay, E. A. Emini, W. A. Schleif, J. R. Huff, P. S. Anderson, J. Med. Chem. 1994, 37, 1177.
- (1994) J. Med. Chem , vol.37 , pp. 1177
- Ghosh, A.K.¹ Lee, H.Y.² Thompson, W.J.³ Culberson, C.⁴ Holloway, M.K.⁵ McKee, S.P.⁶ Munson, P.M.⁷ Duong, T.T.⁸ Smith, A.M.⁹ Darke, P.L.¹⁰ Zugay, J.A.¹¹ Emini, E.A.¹² Schleif, W.A.¹³ Huff, J.R.¹⁴ Anderson, P.S.¹⁵

25
- 12344285811
- a) D. Hoppe, H. Paulsen, Tetrahedron 1992, 48, 5667;
- (1992) Tetrahedron , vol.48 , pp. 5667
- Hoppe, D.¹ Paulsen, H.²

26
- 84985649743
- b) D. Hoppe, B. Peschke, J. Lüßmann, M. Dyrbusch, Chem. Ber. 1992, 125, 1421;
- (1992) Chem. Ber , vol.125 , pp. 1421
- Hoppe, D.¹ Peschke, B.² Lüßmann, J.³ Dyrbusch, M.⁴

27
- 0000832426
- c) S. Sengupta, V. Snieckus, J. Org. Chem. 1990, 55, 5680;
- (1990) J. Org. Chem , vol.55 , pp. 5680
- Sengupta, S.¹ Snieckus, V.²

28
- 85032754032
- d) P. Kocienski, N. J. Dixon, Synlett 1989, 52.
- (1989) Synlett , pp. 52
- Kocienski, P.¹ Dixon, N.J.²

29
- 34447304537
- a) D. Hoppe, E. Beckmann, Synthesis 2005, 217;
- (2005) Synthesis , pp. 217
- Hoppe, D.¹ Beckmann, E.²

30
- 34447297999
- b) D. Hoppe, E. Beckmann, V. Desai, Synlett 2004, 2275.
- (2004) Synlett , pp. 2275
- Hoppe, D.¹ Beckmann, E.² Desai, V.³

31
- 0001416422
- a) D. H. R. Barton, G. Bashiardes, J.-L. Fourrey, Tetrahedron Lett. 1983, 24, 1605;
- (1983) Tetrahedron Lett , vol.24 , pp. 1605
- Barton, D.H.R.¹ Bashiardes, G.² Fourrey, J.-L.³

32
- 0000256044
- b) J. M. MacDougall, V. J. Santora, S. K. Verma, P. Turnbull, C. R. Hernandez, H. W. Moore, J. Org. Chem. 1998, 63, 6905;
- (1998) J. Org. Chem , vol.63 , pp. 6905
- MacDougall, J.M.¹ Santora, V.J.² Verma, S.K.³ Turnbull, P.⁴ Hernandez, C.R.⁵ Moore, H.W.⁶

33
- 0344951058
- c) X. J. Wang, S. A. Hart, B. Xu, M. D. Mason, F. A. Etzkorn, J. Org. Chem. 2003, 68, 2343.
- (2003) J. Org. Chem , vol.68 , pp. 2343
- Wang, X.J.¹ Hart, S.A.² Xu, B.³ Mason, M.D.⁴ Etzkorn, F.A.⁵

34
- 33947468884
- H. E. Zimmerman, D. M. Traxler, J. Am. Chem. Soc. 1957, 79, 1920.
- (1957) J. Am. Chem. Soc , vol.79 , pp. 1920
- Zimmerman, H.E.¹ Traxler, D.M.²

35
- 33746630674
- D. Hoppe, M. Seppi, R. Kalkofen, J. Reupohl, R. Fröhlich, Angew. Chem. 2004, 116, 1447;
- (2004) Angew. Chem , vol.116 , pp. 1447
- Hoppe, D.¹ Seppi, M.² Kalkofen, R.³ Reupohl, J.⁴ Fröhlich, R.⁵

36
- 4544265506
- Angew. Chem. Int. Ed. 2004, 43, 1423.
- (2004) Chem. Int. Ed , vol.43 , pp. 1423
- Angew¹

37
- 34447301946
- Dissertation, University of Münster
- J. Reuber, Dissertation, University of Münster, 2004;
- (2004)
- Reuber, J.¹

38
- 34447338507
- Dissertation, University of Münster
- R. Kalkofen, Dissertation, University of Münster, 2005.
- (2005)
- Kalkofen, R.¹

39
- 34447327724
- X-ray crystal structure analysis for 21c: formula C 18H33NO3, M, 311.45, colorless crystal 0.35 X 0.30 X 0.25 mm, a, 9.378(1, b, 11.460(1, c, 18.439(1) Å, V, 1981.7(3) Å3, ρcalc, 1.044 g cm-3, μ, 0.550 mm-1, empirical absorption correction (0.831 ≤ T ≤ 0.875, Z, 4, orthorhombic, space group P212121 (No. 19, λ, 1.54178 Å, T, 223 K, ω and φ scans, 9108 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 3287 independent (Rint, 0.030) and 3210 observed reflections [I ≥ 2σ(I, 208 refined parameters, R, 0.032, wR 2, 0.087, Flack parameter -0.1(2, max. residual electron density 0.11, 0.11) e Å-3
- -3, hydrogen atoms calculated and refined as riding atoms.

40
- 34447322955
- Data sets were collected with Nonius KappaCCD diffractometers, in case of Mo-radiation equipped with a rotating anode generator. Programs used: COLLECT (Nonius B. V., 1998) for data collection, Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326)
- Data sets were collected with Nonius KappaCCD diffractometers, in case of Mo-radiation equipped with a rotating anode generator. Programs used: COLLECT (Nonius B. V., 1998) for data collection, Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326)

41
- 84977289324
- for data reduction, SORTAV R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37;
- for data reduction, SORTAV (R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33-37;

42
- 0642270732
- R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426)
- (1997) J. Appl. Crystallogr , vol.30 , pp. 421-426
- Blessing, R.H.¹

43
- 0038414570
- and Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr., Sect. A 2003, 59, 228-234)
- and Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr., Sect. A 2003, 59, 228-234)

44
- 84943920736
- for absorption correction, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473)
- for absorption correction, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473)

45
- 34447299838
- for structure solution, SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997) for structure refinement, SCHAKAL (E. Keller, University of Freiburg, 1997) for graphics. CCDC-636950 to -636953 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.
- for structure solution, SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997) for structure refinement, SCHAKAL (E. Keller, University of Freiburg, 1997) for graphics. CCDC-636950 to -636953 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.

46
- 34447309492
- X-ray crystal structure analysis for (S,S,Z)-21d: formula C22H32BrNO3, M, 438.40, colorless crystal 0.60 X 0.15 X 0.10 mm, a, 8.426(1, b, 9.016(1, c, 15.375(1) Å, β, 94.57(1, V, 1164.3(2) Å3, ρcalc, 1.250 g cm-3, μ, 2.557 mm-1, empirical absorption correction (0.309 ≤ T ≤ 0.784, Z, 2, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K, ω and φ scans, 6367 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.58 Å-1, 2631 independent (Rint, 0.043) and 2584 observed reflections [I ≥ 2σ(I, 253 refined parameters, R, 0.042, wR 2, 0.116, Flack parameter 0.05(3, max. residual electron density 0.43, 0.37) e Å
- -3, hydrogen atoms calculated and refined as riding atoms.

47
- 0000442078
- D. Hoppe, R. Hanko, Angew. Chem. 1982, 94, 378;
- (1982) Angew. Chem , vol.94 , pp. 378
- Hoppe, D.¹ Hanko, R.²

48
- 84981963737
- Angew. Chem. Int. Ed. Engl. 1982, 21, 372.
- (1982) Angew. Chem. Int. Ed. Engl , vol.21 , pp. 372

49
- 0030040452
- H. Paulsen, C. Graeve, D. Hoppe, Synthesis 1996, 141.
- (1996) Synthesis , pp. 141
- Paulsen, H.¹ Graeve, C.² Hoppe, D.³

50
- 34447320945
- X-ray crystal structure analysis for (S,1Z,2E, 25b: formula C23H39NO3, M, 377.55, colorless crystal 0.45 X 0.35 X 0.20 mm, a, 11.110(1, b, 11.204(1, c, 18.863(1) Å, V, 2348.0(3) Å3, ρcalc, 1.068 g cm-3, μ, 0.069 mm-1, empirical absorption correction (0.970 ≤ T ≤ 0.986, Z, 4, orthorhombic, space group P212 121 (No. 19, λ, 0.71073 Å, T, 198 K, ω and φ scans, 18301 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.67 Å-1, 5671 independent (Rint, 0.079) and 3142 observed reflections [I ≥ 2σ(I, 253 refined parameters, R, 0.075, wR2, 0.229, Flack parameter -12, max. residual electron densi
- -3, hydrogen atoms calculated and refined as riding atoms.

51
- 34447331602
- X-ray crystal structure analysis for (R,R,1Z,2E, 28c: formula C25H36BrNO3, M, 478.46, colorless crystal 0.30 X 0.15 X 0.15 mm, a, 6.522(1, b, 12.719(1, c, 15.109(1) Å, β, 97.46(1, V, 1242.7(2) Å3, ρcalc, 1.279 g cm-3, μ, 1.678 mm-1, empirical absorption correction (0.633 ≤ T ≤ 0.787, Z, 2, monoclinic, space group P2 1 (No. 4, λ, 0.71073 Å, T, 198 K, ω and φ scans, 10810 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.67 Å-1, 5368 independent (Rint, 0.061) and 3590 observed reflections [I ≥ 2σ(I, 278 refined parameters, R, 0.053, wR2, 0.113, Flack parameter 0.021, max. residual electron density 0
- -3, hydrogen atoms calculated and refined as riding atoms.

52
- 0000760349
- a) M. Schlosser, G. Rauchschwalbe, J. Am. Chem. Soc. 1978, 100, 3258;
- (1978) J. Am. Chem. Soc , vol.100 , pp. 3258
- Schlosser, M.¹ Rauchschwalbe, G.²

53
- 0000939579
- b) A. Nakamura, H. Yasuda, M. Yamauchi, Y. Ohnuma, Bull. Chem. Soc. Jpn. 1981, 54, 1481.
- (1981) Bull. Chem. Soc. Jpn , vol.54 , pp. 1481
- Nakamura, A.¹ Yasuda, H.² Yamauchi, M.³ Ohnuma, Y.⁴

54
- 34447335248
- a) M. T. Reetz, R. Urz, T. Schuster, Synthesis 1985, 540;
- (1985) Synthesis , pp. 540
- Reetz, M.T.¹ Urz, R.² Schuster, T.³

55
- 84981821558
- b) E. P. Benzing, W. A. Kornicker, Chem. Ber. 1961, 94, 2263.
- (1961) Chem. Ber , vol.94 , pp. 2263
- Benzing, E.P.¹ Kornicker, W.A.²

56
- 34447323219
- Dissertation, University of Kiel
- T. Krämer, Dissertation, University of Kiel, 1989.
- (1989)
- Krämer, T.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.