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Volumn , Issue 20, 2007, Pages 3337-3348

Asymmetric homoaldol reactions with cyclohex-2-enyl N,N- diisopropylcarbamate: Kinetic resolution, elucidation of the stereochemical course and applications in the synthesis of hexahydroisobenzofuran-4-(1H)-ones

(4) Becker, Jochen a Fröhlich, Roland a Salorinne, Kirsi b Hoppe, Dieter a

a UNIVERSITY OF MÜNSTER (Germany)

b UNIVERSITY OF JYVÄSKYLÄ (Finland)

Author keywords

Asymmetric synthesis; Homoaldol reactions; Kinetic resolution; Metallated allyl carbamates; Tetrahydrofuran synthesis

Indexed keywords

EID: 34447542845 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.200700219 Document Type: Article

Times cited : (22)

References (51)

1
- 0000854142
- For reviews, see: a
- For reviews, see: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410;
- (1997) Angew. Chem , vol.109 , pp. 2376-2410
- Hoppe, D.¹ Hense, T.²

2
- 0030694010
- Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
- (1997) Angew. Chem. Int. Ed. Engl , vol.36 , pp. 2282-2316

3
- 0033020763
- b) H. Ahlbrecht, U. Beyer, Synthesis 1999, 365-390;
- (1999) Synthesis , pp. 365-390
- Ahlbrecht, H.¹ Beyer, U.²

4
- 0037585195
- Organolithiums in Enantioselective Synthesis
- Ed, D. M. Hodgson, Springer, Berlin
- c) D. Hoppe, F. Marr, M. Brüggemann, Organolithiums in Enantioselective Synthesis in Top. Organomet. Chem. (Ed.: D. M. Hodgson), Springer, Berlin, 2003, vol. 5, pp. 61-138;
- (2003) Top. Organomet. Chem , vol.5 , pp. 61-138
- Hoppe, D.¹ Marr, F.² Brüggemann, M.³

5
- 0842300569
- Organolithiums in Enantioselective Synthesis
- Ed, D. M. Hodgson, Springer, Berlin
- d) P. Beak, T. A. Johnson, D. D. Kim, S. H. Lim, Organolithiums in Enantioselective Synthesis in Top. Organomet. Chem. (Ed.: D. M. Hodgson), Springer, Berlin, 2003, vol. 5, pp. 139-176;
- (2003) Top. Organomet. Chem , vol.5 , pp. 139-176
- Beak, P.¹ Johnson, T.A.² Kim, D.D.³ Lim, S.H.⁴

6
- 18844423506
- Eds, Z. Rappoport, I. Marek, Wiley, Chichester
- e) D. Hoppe, G. Christoph in The Chemistry of Organolithium Compounds (Eds.: Z. Rappoport, I. Marek), Wiley, Chichester, 2004, vol. 2, pp. 1055-1164.
- (2004) The Chemistry of Organolithium Compounds , vol.2 , pp. 1055-1164
- Hoppe, D.¹ Christoph, G.²

7
- 34447534117
- Recent examples: a D. Hoppe, M. Özlügedik, J. Kristensen, B. Wibbeling, R. Fröhlich, Eur. J. Org. Chem. 2002, 414-427;
- Recent examples: a) D. Hoppe, M. Özlügedik, J. Kristensen, B. Wibbeling, R. Fröhlich, Eur. J. Org. Chem. 2002, 414-427;

8
- 7044261570
- b) M. Seppi, R. Kalkofen, J. Reupohl, R. Fröhlich, D. Hoppe, Angew. Chem. 2004, 116, 1447-1451;
- (2004) Angew. Chem , vol.116 , pp. 1447-1451
- Seppi, M.¹ Kalkofen, R.² Reupohl, J.³ Fröhlich, R.⁴ Hoppe, D.⁵

9
- 4544265506
- Angew. Chem. Int. Ed. 2004, 43, 1423-1427;
- (2004) Chem. Int. Ed , vol.43 , pp. 1423-1427
- Angew¹

10
- 12144287279
- c) J. Reuber, R. Fröhlich, D. Hoppe, Org. Lett. 2004, 6, 783-786;
- (2004) Org. Lett , vol.6 , pp. 783-786
- Reuber, J.¹ Fröhlich, R.² Hoppe, D.³

11
- 33746592076
- d) R. Bou Chedid, R. Fröhlich, D. Hoppe, Org. Lett. 2006, 8, 3061-3064.
- (2006) Org. Lett , vol.8 , pp. 3061-3064
- Bou Chedid, R.¹ Fröhlich, R.² Hoppe, D.³

12
- 34447534118
- J. Becker, S. Grimme, R. Fröhlich, D. Hoppe, Angew. Chem. 2007, 119, 1672-1676;
- (2007) Angew. Chem , vol.119 , pp. 1672-1676
- Becker, J.¹ Grimme, S.² Fröhlich, R.³ Hoppe, D.⁴

13
- 34248226223
- Angew. Chem. Int. Ed. 2007, 46, 1645-1649.
- (2007) Chem. Int. Ed , vol.46 , pp. 1645-1649
- Angew¹

14
- 0343892179
- J. A. Marshall, S. B. DeHoff, Tetrahedron Lett. 1986, 27, 4873-4876.
- (1986) Tetrahedron Lett , vol.27 , pp. 4873-4876
- Marshall, J.A.¹ DeHoff, S.B.²

15
- 0000579461
- C. L. Kissel, B. Rickborn, J. Org. Chem. 1972, 37, 2060-2063.
- (1972) J. Org. Chem , vol.37 , pp. 2060-2063
- Kissel, C.L.¹ Rickborn, B.²

16
- 17444431613
- N. Holub, J. Neidhöfer, S. Blechert, Org. Lett. 2005, 7, 1227-1229.
- (2005) Org. Lett , vol.7 , pp. 1227-1229
- Holub, N.¹ Neidhöfer, J.² Blechert, S.³

17
- 0032556198
- M. K. Södergren, P. G. Andersson, J. Am. Chem. Soc. 1998, 120, 10760-10761.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 10760-10761
- Södergren, M.K.¹ Andersson, P.G.²

18
- 0032706536
- G. A. Weisenburger, N. C. Faibish, D. J. Pippel, P. Beak, J. Am. Chem. Soc. 1999, 121, 9522-9530.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 9522-9530
- Weisenburger, G.A.¹ Faibish, N.C.² Pippel, D.J.³ Beak, P.⁴

19
- 34447564803
- For kinetic resolution of open-chained carbamates by nBuLi/(-)- sparteine (9) see: a) O. Zschage, J.-R. Schwark, D. Hoppe, Angew. Chem. 1990, 102, 336-337;
- For kinetic resolution of open-chained carbamates by nBuLi/(-)- sparteine (9) see: a) O. Zschage, J.-R. Schwark, D. Hoppe, Angew. Chem. 1990, 102, 336-337;

20
- 0025309871
- Angew. Chem. Int. Ed. Engl. 1990, 29, 296-298;
- (1990) Angew. Chem. Int. Ed. Engl , vol.29 , pp. 296-298

21
- 0026754759
- b) O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 1992, 48, 8377-8388;
- (1992) Tetrahedron , vol.48 , pp. 8377-8388
- Zschage, O.¹ Schwark, J.-R.² Krämer, T.³ Hoppe, D.⁴

22
- 0026644342
- c) O. Zschage, J.-R. Schwark, T. Krämer, D. Hoppe, Tetrahedron 1992, 48, 8389-8392.
- (1992) Tetrahedron , vol.48 , pp. 8389-8392
- Zschage, O.¹ Schwark, J.-R.² Krämer, T.³ Hoppe, D.⁴

23
- 0345469752
- For kinetic resolution of allyltitanium carbamates by chiral aldehydes, see: a
- For kinetic resolution of allyltitanium carbamates by chiral aldehydes, see: a) R. W. Hoffmann, J. Lanz, R. Metternich, G. Tarara, D. Hoppe, Angew. Chem. 1987, 99, 1196-1197;
- (1987) Angew. Chem , vol.99 , pp. 1196-1197
- Hoffmann, R.W.¹ Lanz, J.² Metternich, R.³ Tarara, G.⁴ Hoppe, D.⁵

24
- 84985502354
- Angew. Chem. Int. Ed. Engl. 1987, 26, 1145-1146;
- (1987) Angew. Chem. Int. Ed. Engl , vol.26 , pp. 1145-1146

25
- 0008346631
- b) I. Berque, P. Le Ménez, P. Razon, C. Anies, A. Pancrazi, J. Ardisson, A. Neuman, T. Prangé, J.-D. Brion, Synlett 1998, 1132-1134;
- (1998) Synlett , pp. 1132-1134
- Berque, I.¹ Le Ménez, P.² Razon, P.³ Anies, C.⁴ Pancrazi, A.⁵ Ardisson, J.⁶ Neuman, A.⁷ Prangé, T.⁸ Brion, J.-D.⁹

26
- 0008374094
- c) I. Berque, P. Le Ménez, P. Razon, C. A. Pancrazi, J. Ardisson, J.-D. Brion, Synlett 1998, 1135-1137;
- (1998) Synlett , pp. 1135-1137
- Berque, I.¹ Le Ménez, P.² Razon, P.³ Pancrazi, C.A.⁴ Ardisson, J.⁵ Brion, J.-D.⁶

27
- 12344264925
- d) P. Razon, S. Dhulut, S. Bezzenine-Lafollée, J. Courtieu, A. Pancrazi, J. Ardisson, Synthesis 2005, 102-108;
- (2005) Synthesis , pp. 102-108
- Razon, P.¹ Dhulut, S.² Bezzenine-Lafollée, S.³ Courtieu, J.⁴ Pancrazi, A.⁵ Ardisson, J.⁶

28
- 34447548470
- application in total synthesis: E. de Lemos, F.-H. Porée, A. Commerçon, J.-F. Betzer, A. Pancrazi, J. Ardisson, Angew. Chem. 2007, 119, 1949-1953;
- application in total synthesis: E. de Lemos, F.-H. Porée, A. Commerçon, J.-F. Betzer, A. Pancrazi, J. Ardisson, Angew. Chem. 2007, 119, 1949-1953;

29
- 34249672439
- [10d]
- [10d]

30
- 0024791574
- a) T. Krämer, J.-R. Schwark, D. Hoppe, Tetrahedron Lett. 1989, 30, 7037-7040;
- (1989) Tetrahedron Lett , vol.30 , pp. 7037-7040
- Krämer, T.¹ Schwark, J.-R.² Hoppe, D.³

31
- 0030030150
- b) H. Paulsen, C. Graeve, R. Fröhlich, D. Hoppe, Synthesis 1996, 1, 145-149.
- (1996) Synthesis , vol.1 , pp. 145-149
- Paulsen, H.¹ Graeve, C.² Fröhlich, R.³ Hoppe, D.⁴

32
- 34447545438
- Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998),
- Data sets were collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998),

33
- 0031059866
- data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology, 1997, 276, 307-326),
- data reduction Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology, 1997, 276, 307-326),

34
- 0038414570
- absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234),
- absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234),

35
- 84943920736
- structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997) , graphics SCHAKAL (E. Keller, University of Freiburg, 1997). CCDC-639293 to -639296 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.
- structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997) , graphics SCHAKAL (E. Keller, University of Freiburg, 1997). CCDC-639293 to -639296 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.

36
- 34447548469
- X-ray crystal structure analysis for 12c: formula C 20H28BrNO3, M, 410.34, colorless crystal 0.10 x 0.05 x 0.03 mm, a, 7.465(1, b, 10.067(1, c, 27.851(1) Å, V, 2093.0(4) Å3, ρcalc, 1.302 g cm-3, μ, 2.810 mm-1, empirical absorption correction (0.766 ≤ T ≤ 0.921, Z, 4, orthorhombic, space group P212121 (No. 19, λ, 1.54178 Å, T, 223 K, ω and φ scans, 8000 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 3039 independent (Rint, 0.060) and 2225 observed reflections [I ≥ 2 σ(I, 231 refined parameters, R, 0.056, wR 2, 0.114, Flack parameter -0.07(4, max. residual electron density 0.32, 0.26) e·A
- -3, hydrogen atoms calculated and refined as riding atoms.

37
- 33947468884
- H. E. Zimmerman, M. D. Traxler, J. Am. Chem. Soc. 1957, 79, 1920-1923.
- (1957) J. Am. Chem. Soc , vol.79 , pp. 1920-1923
- Zimmerman, H.E.¹ Traxler, M.D.²

38
- 0000928950
- a) D. Hoppe, T. Krämer, C. Freire Erdbrügger, E. Egert, Tetrahedron Lett. 1989, 30, 1233-1236;
- (1989) Tetrahedron Lett , vol.30 , pp. 1233-1236
- Hoppe, D.¹ Krämer, T.² Freire Erdbrügger, C.³ Egert, E.⁴

39
- 27544464237
- b) S. Ünaldi, M. Özlügedik, R. Fröhlich, D. Hoppe, Adv. Synth. Catal. 2005, 347, 1621-1626.
- (2005) Adv. Synth. Catal , vol.347 , pp. 1621-1626
- Ünaldi, S.¹ Özlügedik, M.² Fröhlich, R.³ Hoppe, D.⁴

40
- 0042229312
- H,H couplings see: Y. Chai, D. A. Vicic, M. C. McIntosh, Org Lett. 2003, 5, 1039-1042.
- H,H couplings see: Y. Chai, D. A. Vicic, M. C. McIntosh, Org Lett. 2003, 5, 1039-1042.

41
- 34447554332
- X-ray crystal structure analysis for ent-22b: formula C18H23BrO2, M, 351.27, colorless crystal 0.15 x 0.03 x 0.03 mm, a, 6.5993(1, b, 31.6292(6, c, 7.7836(1) Å, β, 90.256(1)°, V, 1624.66(4) Å3, ρcalc, 1.436 g cm-3, μ, 3.457 mm-1, empirical absorption correction (0.625 ≤ T ≤ 0.903, Z, 4, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K, ω and φ scans, 6351 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 4030 independent (Rint, 0.050) and 3832 observed reflections [I ≥ 2 σ(I, 385 refined parameters, R, 0.049, wR 2, 0.132, Flack parameter 0.03(3, max. residual electron density 0.97, 0.36) e·
- -3, two almost identical molecules in the asymmetric unit, hydrogen atoms calculated and refined as riding atoms.

42
- 34447568104
- X-ray crystal structure analysis for 22f: formula C 27H30O2, M, 386.51, colorless crystal 0.40 x 0.25 x 0.10 mm, a, 6.907(1, b, 8.946(1, c, 16.886(1) Å, β, 96.83(1)°, V, 1036.0(2) Å3, ρcalc, 1.239 g cm-3, μ, 0.590 mm-1, empirical absorption correction (0.798 ≤ T ≤ 0.943, Z, 2, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K, ω and φ scans, 8144 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 2652 independent (Rint, 0.030) and 2622 observed reflections [I ≥ 2 σ(I, 264 refined parameters, R, 0.035, wR 2, 0.093, Flack parameter 0.0(3, max. residual electron density 0.12, 0.11) e·Å
- -3, hydrogen atoms calculated and refined as riding atoms.

43
- 34447556571
- 19] X-ray crystal structure analysis for 22g: formula C 27H30O2, M, 386.51, colorless crystal 0.20 x 0.20 x 0.15 mm, a, 6.479(1, b, 8.790(1, c, 18.784(1) Å, β, 98.24(1)°, V, 1058.7(2) Å3, ρcalcd, 1-212 g cm-3, μ, 0.577 mm-1, empirical absorption correction (0.893 ≤ T ≤ 0.918, Z, 2, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K, ω and φ scans, 11912 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 3613 independent (Rint, 0.048) and 3226 observed reflections [I ≥ 2 σ(I, 264 refined parameters, R, 0.070, wR 2, 0.190, Flack parameter -0.4(5, max. residual electron density 0.13, 0.15) e·Å
- -3, hydrogen atoms calculated and refined as riding atoms.

44
- 34447559472
- following article
- J. Becker, R. Fröhlich, O. Kataeva, D. Hoppe, Eur. J. Org. Chem. 2007, 3349-3364, following article.
- (2007) Eur. J. Org. Chem , pp. 3349-3364
- Becker, J.¹ Fröhlich, R.² Kataeva, O.³ Hoppe, D.⁴

45
- 33845280542
- C. Benson, P. Cai, M. Colon, M. A. Haiza, M. Tokles, J. K. Snyder, J. Org. Chem. 1988, 53, 5335-5341.
- (1988) J. Org. Chem , vol.53 , pp. 5335-5341
- Benson, C.¹ Cai, P.² Colon, M.³ Haiza, M.A.⁴ Tokles, M.⁵ Snyder, J.K.⁶

46
- 33847799858
- W. G. Konfron, L. M. Baclawski, J. Org. Chem. 1976, 41, 1879-1880.
- (1976) J. Org. Chem , vol.41 , pp. 1879-1880
- Konfron, W.G.¹ Baclawski, L.M.²

47
- 0000898481
- D. Hoppe, R. Hanko, A. Brönneke, F. Lichtenberg, E. van Hülsen, Chem. Ber. 1985, 118, 2822-2851.
- (1985) Chem. Ber , vol.118 , pp. 2822-2851
- Hoppe, D.¹ Hanko, R.² Brönneke, A.³ Lichtenberg, F.⁴ van Hülsen, E.⁵

48
- 34447566838
- Samples of the crystalline product had 23% ee (HPLC), the oily residue had 94% ee (HPLC).
- Samples of the crystalline product had 23% ee (HPLC), the oily residue had 94% ee (HPLC).

49
- 34447555561
- 4 by atmospheric moisture.
- 4 by atmospheric moisture.

50
- 34447578567
- In order to remove all traces of the liberated stannanes the crude products were purified two times by flash column chromatography
- In order to remove all traces of the liberated stannanes the crude products were purified two times by flash column chromatography.

51
- 34447576354
- The diastereomeric ratio was determined from the crude products by GC (HP-5).
- The diastereomeric ratio was determined from the crude products by GC (HP-5).

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