SCOPUS 정보 검색 플랫폼

Volumn , Issue 20, 2007, Pages 3349-3364

Stereoselective synthesis of hexahydroisobenzofuran-4(1H)-ones from chiral substituted cyclohex-2-enyl carbamates via asymmetric homoaldol reaction and THF cyclocondensation

(4) Becker, Jochen a Fröhlich, Roland a Kataeva, Olga a Hoppe, Dieter a

a UNIVERSITY OF MÜNSTER (Germany)

Author keywords

Asymmetric synthesis; Heterocycles; Homoaldol reactions; Metallated allyl carbamates; Tetrahydrofuran synthesis

Indexed keywords

EID: 34447559472 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.200700220 Document Type: Article

Times cited : (8)

References (55)

1
- 0032585375
- Reviews: a
- Reviews: a) P. Bernadelli, L. A. Paquette, Heterocycles 1998, 49, 531-556;
- (1998) Heterocycles , vol.49 , pp. 531-556
- Bernadelli, P.¹ Paquette, L.A.²

2
- 0036727043
- b) P.-S. Sung, M.-C. Chen, Heterocycles 2002, 57, 1705-1715.
- (2002) Heterocycles , vol.57 , pp. 1705-1715
- Sung, P.-S.¹ Chen, M.-C.²

3
- 0035913732
- Total synthesis: a P. Bernadelli, O. M. Moradei, D. Friedrich, J. Yang, F. Gallou, B. P. Dyck, R. W. Doskotch, T. Lange, L. A. Paquette, J. Am. Chem. Soc. 2001, 123, 9021-9032;
- Total synthesis: a) P. Bernadelli, O. M. Moradei, D. Friedrich, J. Yang, F. Gallou, B. P. Dyck, R. W. Doskotch, T. Lange, L. A. Paquette, J. Am. Chem. Soc. 2001, 123, 9021-9032;

4
- 0035913709
- b) D. W. C. MacMillan, L. E. Overman, L. D. Pennington, J. Am. Chem. Soc. 2001, 123, 9033-9044.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 9033-9044
- MacMillan, D.W.C.¹ Overman, L.E.² Pennington, L.D.³

5
- 0038547883
- Total synthesis: O. Corminboeuf, L. E. Overman, L. D. Pennington, J. Am. Chem. Soc. 2003, 125, 6650-6652.
- Total synthesis: O. Corminboeuf, L. E. Overman, L. D. Pennington, J. Am. Chem. Soc. 2003, 125, 6650-6652.

6
- 0037144643
- a) M. E. Jung, J. Pontillo, J. Org. Chem. 2002, 67, 6848-6851;
- (2002) J. Org. Chem , vol.67 , pp. 6848-6851
- Jung, M.E.¹ Pontillo, J.²

7
- 0037424852
- b) M. E. Jung, J. Pontillo, Tetrahedron 2003, 59, 2729-2736;
- (2003) Tetrahedron , vol.59 , pp. 2729-2736
- Jung, M.E.¹ Pontillo, J.²

8
- 0042229312
- c) Y. Chai, D. A. Vicic, M. C. McIntosh, Org. Lett. 2003, 5, 1039-1042;
- (2003) Org. Lett , vol.5 , pp. 1039-1042
- Chai, Y.¹ Vicic, D.A.² McIntosh, M.C.³

9
- 24944507270
- d) T. Akindele, S. P. Marsden, J. G. Cumming, Tetrahedron Lett. 2005, 46, 7235-7238.
- (2005) Tetrahedron Lett , vol.46 , pp. 7235-7238
- Akindele, T.¹ Marsden, S.P.² Cumming, J.G.³

10
- 34447542845
- preceding article
- J. Becker, R. Fröhlich, K. Salorinne, D. Hoppe, Eur. J. Org. Chem. 2007, 3337-3348, preceding article.
- (2007) Eur. J. Org. Chem , pp. 3337-3348
- Becker, J.¹ Fröhlich, R.² Salorinne, K.³ Hoppe, D.⁴

11
- 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

12
- 34248226223
- Angew. Chem. Int. Ed. 2007, 46, 1645-1649.
- (2007) Chem. Int. Ed , vol.46 , pp. 1645-1649
- Angew¹

13
- 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

14
- 0030694010
- Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
- (1997) Angew. Chem. Int. Ed. Engl , vol.36 , pp. 2282-2316

15
- 0033020763
- b) H. Ahlbrecht, U. Beyer, Synthesis 1999, 365-390;
- (1999) Synthesis , pp. 365-390
- Ahlbrecht, H.¹ Beyer, U.²

16
- 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

17
- 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

18
- 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

19
- 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

20
- 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

21
- 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

22
- 0000428861
- P. van Eikeren, L. Garver, J. Org. Chem. 1976, 41, 2773-2774.
- (1976) J. Org. Chem , vol.41 , pp. 2773-2774
- van Eikeren, P.¹ Garver, L.²

23
- 0037130642
- Synthesis of enantiomerically pure (R)-(-)-crypton: a) J. Evarts, E. Torres, P. L. Fuchs, J. Am. Chem. Soc. 2002, 124, 11093-11101;
- Synthesis of enantiomerically pure (R)-(-)-crypton: a) J. Evarts, E. Torres, P. L. Fuchs, J. Am. Chem. Soc. 2002, 124, 11093-11101;

24
- 0042179715
- rac-crypton (<5% ee) from nopinon and reduction: b) J. M. Coxon, G. J. Hydes, P. J. Steel, Tetrahedron 1985, 41, 5213-5217;
- rac-crypton (<5% ee) from nopinon and reduction: b) J. M. Coxon, G. J. Hydes, P. J. Steel, Tetrahedron 1985, 41, 5213-5217;

25
- 0025309685
- c) H. C. Brown, S. A. Weissman, P. T. Perumal, U. P. Dhokte, J. Org. Chem. 1990, 55, 1217-1223.
- (1990) J. Org. Chem , vol.55 , pp. 1217-1223
- Brown, H.C.¹ Weissman, S.A.² Perumal, P.T.³ Dhokte, U.P.⁴

26
- 34447506982
- Data sets were collected with an Enraf-Nonius CAD4 and a Nonius KappaCCD diffractometers. Programs used: data collection EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology, 1997, 276, 307-326),
- Data sets were collected with an Enraf-Nonius CAD4 and a Nonius KappaCCD diffractometers. Programs used: data collection EXPRESS (Nonius B. V., 1994) and COLLECT (Nonius B. V., 1998), data reduction MolEN (K. Fair, Enraf-Nonius B. V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods in Enzymology, 1997, 276, 307-326),

27
- 0038414570
- absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. Ser. A 2003, 59, 228-234),
- absorption correction Denzo (Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. Ser. A 2003, 59, 228-234),

28
- 84943920736
- structure solution SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Ser. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics SCHAKAL (E. Keller, University of Freiburg, 1997). CCDC-639288 to -639292 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. Ser. A 1990, 46, 467-473), structure refinement SHELXL-97 (G. M. Sheldrick, University of Göttingen, 1997), graphics SCHAKAL (E. Keller, University of Freiburg, 1997). CCDC-639288 to -639292 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.

29
- 34447504278
- X-ray crystal structure analysis for 11b: formula C 30H39NO3, M, 461.62, colorless crystal 0.45 x 0.20 x 0.20 mm, a, 7.728(1, b, 10.606(1, c, 32.505(4) Å, V, 2664.2(5) Å3, ρcalc, 1.151 g cm-3, μ, 0.572 mm-1, empirical absorption correction (0.783 ≤ T ≤ 0.894, Z, 4, orthorhombic, space group P212121 (No. 19, λ, 1.54178 Å, T, 223 K, ω/2θ scans, 3121 reflections collected, h, k, l, sin9)/λ, 0.62 Å-1, 3121 independent and 2227 observed reflections [I ≥ 2 σ(I, 315 refined parameters, R, 0.048, wR2, 0.145, Flack parameter 0.1(5, max. residual electron density 0.21, 0.20) e Å-3, hydrogen atoms calculated and refined as riding atoms
- -3, hydrogen atoms calculated and refined as riding atoms.

30
- 12344264925
- 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

31
- 12344297631
- P. Razon, M.-A. N'Zoutani, S. Dhulut, S. Bezzenine-Lafollée, A. Pancrazi, J. Ardisson, Synthesis 2005, 109-121.
- (2005) Synthesis , pp. 109-121
- Razon, P.¹ N'Zoutani, M.-A.² Dhulut, S.³ Bezzenine-Lafollée, S.⁴ Pancrazi, A.⁵ Ardisson, J.⁶

32
- 0002291128
- a) B. Weidmann, D. Seebach, Angew. Chem. 1983, 95, 12-26;
- (1983) Angew. Chem , vol.95 , pp. 12-26
- Weidmann, B.¹ Seebach, D.²

33
- 33745369627
- Angew. Chem. Int. Ed. Engl. 1983, 22, 31-45;
- (1983) Angew. Chem. Int. Ed. Engl , vol.22 , pp. 31-45

34
- 0242632891
- Ed, M. Schlosser, Wiley-VCH, Chichester, 2nd ed, pp
- b) M. T. Reetz in Organometallics in Synthesis (Ed.: M. Schlosser), Wiley-VCH, Chichester, 2002, 2nd ed., pp. 817-923;
- (2002) Organometallics in Synthesis , pp. 817-923
- Reetz, M.T.¹

35
- 0038455271
- Wiley-VCH, Weinheim
- c) J. Szymoniak, C. Moïse in Titanium and Zirconium in Organic Synthesis, Wiley-VCH, Weinheim 2002, pp. 451-474.
- (2002) Titanium and Zirconium in Organic Synthesis , pp. 451-474
- Szymoniak, J.¹ Moïse, C.²

36
- 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

37
- 0030951974
- S. Hikichi, Y. Gao, F. Sato, Tetrahedron Lett. 1997, 38, 2867-2870.
- (1997) Tetrahedron Lett , vol.38 , pp. 2867-2870
- Hikichi, S.¹ Gao, Y.² Sato, F.³

38
- 0000945611
- a) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, W. Ito, J. Am. Chem. Soc. 1986, 108, 7778;
- (1986) J. Am. Chem. Soc , vol.108 , pp. 7778
- Yamamoto, Y.¹ Nishii, S.² Maruyama, K.³ Komatsu, T.⁴ Ito, W.⁵

39
- 0029582657
- b) Y. Gao, F. Sato, J. Org. Chem. 1995, 60, 8136-8137.
- (1995) J. Org. Chem , vol.60 , pp. 8136-8137
- Gao, Y.¹ Sato, F.²

40
- 0029153281
- J. Szymoniak, H. Lefranc, J. Besancon, C. Moïse, Synthesis 1995, 815-819.
- (1995) Synthesis , pp. 815-819
- Szymoniak, J.¹ Lefranc, H.² Besancon, J.³ Moïse, C.⁴

41
- 34447505434
- A boat-like transition state in which the substituent R occupies an equatorial position would lead to eclipsed interactions with the y-substituents of the allyl carbamate. The chair-like transition states TS-16 and TS-29 explain, why the yields of the homoaldol reactions with sterically demanding alkanals in contrast to arylic aldehydes are better for 3 than for β-methyl-substituted carbamate 2, where the 1,3-diaxial interactions are much larger.
- A boat-like transition state in which the substituent R occupies an equatorial position would lead to eclipsed interactions with the y-substituents of the allyl carbamate. The chair-like transition states TS-16 and TS-29 explain, why the yields of the homoaldol reactions with sterically demanding alkanals in contrast to arylic aldehydes are better for 3 than for β-methyl-substituted carbamate 2, where the 1,3-diaxial interactions are much larger.

42
- 0001153549
- A boat-like transition state was proposed for several titanium-mediated aldol reactions with persubstituted enolates, see: a S. Yamago, D. Machii, E. Nakamura, J. Org. Chem. 1991, 56, 2098-2106;
- A boat-like transition state was proposed for several titanium-mediated aldol reactions with persubstituted enolates, see: a) S. Yamago, D. Machii, E. Nakamura, J. Org. Chem. 1991, 56, 2098-2106;

43
- 0001323711
- b) R. Duthaler, A. Hafner, Chem. Rev. 1992, 92, 807-832.
- (1992) Chem. Rev , vol.92 , pp. 807-832
- Duthaler, R.¹ Hafner, A.²

44
- 34447525931
- Diploma Thesis, University of Münster
- J. Becker, Diploma Thesis, University of Münster, 2005.
- (2005)
- Becker, J.¹

45
- 0011229374
- For the reversal of anti to syn diastereoselectivity in a) crotyltitanium or b) tiglyltitanocene reactions, see: a J. Szymoniak, N. Thery, C. Moïse, Synlett 1997, 1239-1240;
- For the reversal of anti to syn diastereoselectivity in a) crotyltitanium or b) tiglyltitanocene reactions, see: a) J. Szymoniak, N. Thery, C. Moïse, Synlett 1997, 1239-1240;

46
- 2342486512
- b) J. Szymoniak, N. Thery, C. Moïse, Bull. Soc. Chim. Fr. 1997, 134, 85-91.
- (1997) Bull. Soc. Chim. Fr , vol.134 , pp. 85-91
- Szymoniak, J.¹ Thery, N.² Moïse, C.³

47
- 34447524389
- X-ray crystal structure analysis for rac-31a: formula C23H35NO3, M, 373.52, colorless crystal 0.50 x 0.25 x 0.05 mm, a, 11.395(1, b, 18.803(6, c, 10.359(1) Å, V, 2219.5(3) Å3, ρcalc, 1.118 g cm-3, μ, 0.572 mm-1, empirical absorption correction (0.763 ≤ T ≤ 0.972, Z, 4, orthorhombic, space group P212121 (No. 19, λ, 1.54178 Å, T, 223 K, ω and φ scans, 9789 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 3647 independent (Rint, 0.041) and 3346 observed reflections [I ≥ 2 σ(I, 251 refined parameters, R, 0.049, wR 2, 0.133, Flack parameter 0.5(3, max. residual electron density 0.12, 0.15) e A
- -3, hydrogen atoms calculated and refined as riding atoms.

48
- 0033601294
- U. Chiacchio, A. Corsaro, G. Gumina, A. Rescifina, D. Iannazzo, A. Piperno, G. Romeo, R. Romeo, J. Org. Chem. 1999, 64, 9321-9327.
- (1999) J. Org. Chem , vol.64 , pp. 9321-9327
- Chiacchio, U.¹ Corsaro, A.² Gumina, G.³ Rescifina, A.⁴ Iannazzo, D.⁵ Piperno, A.⁶ Romeo, G.⁷ Romeo, R.⁸

49
- 34447506980
- X-ray crystal structure analysis for 38a: formula C 28H28O2, M, 396.50, colorless crystal 0.55 x 0.15 x 0.06 mm, a, 8.811(1, b, 12.110(1, c, 11.188(1) Å, β, 110.23(1)°, V, 1120.1(2) Å3, ρcalc, 1.176 g cm-3, μ, 0.561 mm-1, empirical absorption correction (0.748 ≤ T ≤ 0.967, Z, 2, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K, ω and ρ scans, 11166 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.58 Å-1, 2749 independent (Rint, 0.051) and 2409 observed reflections [I ≥ 2σ(I, 273 refined parameters, R, 0.041, wR 2, 0.110, Flack parameter -0.2(4, max. residual electron density 0.10, 0.11) e Å-3
- -3, hydrogen atoms calculated and refined as riding atoms.

50
- 34447540638
- X-ray crystal structure analysis for 41a: formula C 23H25BrO2, M, 413.34, colorless crystal 0.45 x 0.10 x 0.10 mm, a, 11.838(1, b, 5.945(1, c, 14.515(1) Å, β, 98.72(1)°, V, 1009.7(2) Å3, ρcalc, 1.360 g cm-3, μ, 2.871 mm-1, empirical absorption correction (0.358 ≤ T ≤ 0.761, Z, 2, monoclinic, space group P21 (No. 4, λ, 1.54178 Å, T, 223 K, ω and ρ scans, 6521 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 2642 independent (Rint, 0.036) and 2560 observed reflections [I ≥ 2σ(I, 237 refined parameters, R, 0.038, wR 2, 0.101, Flack parameter 0.07(2, max. residual electron density 0.32, 0.45) e Å-3
- -3, hydrogen atoms calculated and refined as riding atoms.

51
- 34447501296
- The relative configuration of rac-41a, which crystallizes in a different space group than 41a, was also determined by X-ray crystal structure analysis: formula C23H25BrO2, M, 413.34, colorless crystal 0.35 x 0.25 x 0.10 mm, a, 38.648(1, b, 11.462(6, c, 17.901(1) Å, V, 7929.8(8) Å3, ρcalc, 1.385 g cm-3, μ, 2.924 mm-1, empirical absorption correction (0.428 ≤ T ≤ 0.759, Z, 16, orthorhombic, space group Fdd2 (No. 43, λ, 1.54178 Å, T, 223 K, ω and φ scans, 8967 reflections collected (±h, ±k, ±l, sinθ)/λ, 0.60 Å-1, 3251 independent (Rint, 0.033) and 3226 observed reflections [I ≥ 2σI, 238 refined parameters, R, 0.028, wR 2, 0
- -3, hydrogen atoms calculated and refined as riding atoms.

52
- 37049046247
- J. W. Conforth, M. E. Firth, J. Chem. Soc. 1958, 1091-1099.
- (1958) J. Chem. Soc , pp. 1091-1099
- Conforth, J.W.¹ Firth, M.E.²

53
- 34447544963
- Besides the pure diastereomers, fractions of diastereomeric mixtures where obtained, which were separated by repeated chromatography
- Besides the pure diastereomers, fractions of diastereomeric mixtures where obtained, which were separated by repeated chromatography.

54
- 34447540639
- 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).

55
- 34447538768
- The concentration of the carbamate solution is critical for good yields. 1.3 equiv. sBuLi can be used in small scale reactions (0.25 mmol), at scales of ≥ 1.0 mmol 1.0 to 1.05 equiv. of carefully titrated sBuLi and rac-26 are recommended for optimum yields.
- The concentration of the carbamate solution is critical for good yields. 1.3 equiv. sBuLi can be used in small scale reactions (0.25 mmol), at scales of ≥ 1.0 mmol 1.0 to 1.05 equiv. of carefully titrated sBuLi and rac-26 are recommended for optimum yields.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.