(-)-Sparteine-mediated stereoselective intramolecular carbolithiation of 4-substituted 5-hexynyl carbamates. Synthesis of enantiopure 1,3- difunctionalized alkylidene cyclopentanes

Journal of Organic Chemistry

Volumn 64, Issue 23, 1999, Pages 8616-8626

  Oestreich, Martin ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CARBAMIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; SPARTEINE;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; ENANTIOMER; MOLECULAR INTERACTION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 0345148448     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991095u     Document Type: Article

References (74)

1. For reviews, see: (a) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, P., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 271-337. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-871. (d) Negishi, E. Pure Appl. Chem. 1981, 53, 2333-2356.
2. For reviews, see: (a) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, P., Stang, P. J., Eds.; Wiley- VCH: Weinheim, Germany, 1998; pp 271-337. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-871. (d) Negishi, E. Pure Appl. Chem. 1981, 53, 2333-2356.
3. For reviews, see: (a) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, P., Stang, P. J., Eds.; Wiley- VCH: Weinheim, Germany, 1998; pp 271-337. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-871. (d) Negishi, E. Pure Appl. Chem. 1981, 53, 2333-2356.
4. For reviews, see: (a) Marek, I.; Normant, J. F. In Metal-catalyzed Cross-coupling Reactions; Diederich, P., Stang, P. J., Eds.; Wiley- VCH: Weinheim, Germany, 1998; pp 271-337. (b) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (c) Normant, J. F.; Alexakis, A. Synthesis 1981, 841-871. (d) Negishi, E. Pure Appl. Chem. 1981, 53, 2333-2356.
5. For a recent review with focus on enantioselective modifications, see: Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544.
6. (a) Klein, S.; Marek, I.; Poisson, J.-F.; Normant, J. F. J. Am. Chem. Soc. 1995, 117, 8853-8854.
7. (b) Norsikian, S.; Marek, I.; Normant, J. F. Tetrahedron Lett. 1997, 38, 7523-7526.
8. (c) Norsikian, S.; Marek, I.; Poisson, J.-F.; Normant, J. F. J. Org. Chem. 1997, 62, 4898-4899.
9. (a) Woltering, M. J.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1764-1766.
10. (b) Woltering, M. J.; Fröhlich, R.; Wibbeling, B.; Hoppe, D. Synlett 1998, 797-800.
11. (c) Hoppe, D.; Woltering, M. J.; Oestreich, M.; Fröhlich, R. Helv. Chim. Acta, in press.
12. (d) Tomooka, K.; Komine, N.; Sasaki, T.; Shimizu, H.; Nakai, T. Tetrahedron Lett. 1998, 39, 9715-9718.
13. (e) For the stereoselective carbolithiation of conjugated double bonds, see: Oestreich, M.; Hoppe, D. Tetrahedron Lett. 1999, 40, 1881-1884.
14. For enantiospecific intramolecular carbolithiations starting from enantiomerically enriched α-amino- and α-oxy-substituted stannanes, see: (a) Coldham, I.; Hufton, R.; Snowden, D. J. Am. Chem. Soc. 1996, 118, 5322-5323. (b) Tomooka, K.; Komine, N.; Nakai, T. Tetrahedron Lett. 1997, 38, 8939-8942. For a diastereofacially controlled intramolecular carbolithiation, see: Krief, A.; Bousbaa, J. Synlett 1996, 1007- 1009.
15. For enantiospecific intramolecular carbolithiations starting from enantiomerically enriched α-amino- and α-oxy-substituted stannanes, see: (a) Coldham, I.; Hufton, R.; Snowden, D. J. Am. Chem. Soc. 1996, 118, 5322-5323. (b) Tomooka, K.; Komine, N.; Nakai, T. Tetrahedron Lett. 1997, 38, 8939-8942. For a diastereofacially controlled intramolecular carbolithiation, see: Krief, A.; Bousbaa, J. Synlett 1996, 1007- 1009.
16. For enantiospecific intramolecular carbolithiations starting from enantiomerically enriched α-amino- and α-oxy-substituted stannanes, see: (a) Coldham, I.; Hufton, R.; Snowden, D. J. Am. Chem. Soc. 1996, 118, 5322-5323. (b) Tomooka, K.; Komine, N.; Nakai, T. Tetrahedron Lett. 1997, 38, 8939-8942. For a diastereofacially controlled intramolecular carbolithiation, see: Krief, A.; Bousbaa, J. Synlett 1996, 1007-1009.
17. For a preliminary communication of our work, see: Oestreich, M.; Fröhlich, R.; Hoppe, D. Tetrahedron Lett. 1998, 39, 1745-1748.
18. (a) Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 29, 1422-1423.
19. For reviews, see: (b) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.
20. (c) Hoppe, D.; Hintze, F.; Tebben, P.; Paetow, M.; Ahrens, H.; Schwerdtfeger, J.; Sommerfeld, P.; Haller, J.; Guarnieri, W.; Kolczewski, S.; Hense, T.; Hoppe, I. Pure Appl. Chem. 1994, 66, 1479-1486.
21. For the asymmetric deprotonation of carbamates derived from amines, see: (d) Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708-9710.
22. (e) Beak, P.; Basu, A.; Gallagher, D. J.; Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552-560.
23. (a) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 2442-2448.
24. (b) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058-6061.
25. (c) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K.; Ovaska, T. V.; Rossi, K.; Thiel, Y.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 5720-5727.
26. (d) Bailey, W. F.; Gavaskar, K. V. Tetrahedron 1994, 50, 5957-5970.
27. See also: (e) Krief, A.; Kenda, B.; Maertens, C.; Remade, B. Tetrahedron 1996, 52, 7465-7473.
28. (f) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191.
29. (a) Bailey, W. F.; Ovaska, T. V.; Leipert, T. K. Tetrahedron Lett. 1989, 30, 3901-3904.
30. (b) Wu, G.; Cederbaum, F. E.; Negishi, E. Tetrahedron Lett. 1990, 31, 493-496.
31. (c) Bailey, W. F.; Ovaska, T. V. Tetrahedron Lett. 1990, 31, 627-630.
32. Bailey, W. F.; Ovaska, T. V. J. Am. Chem. Soc. 1993, 115, 3080-3090.
33. (a) For a first report, see: Ward, H. R. J. Am. Chem. Soc. 1967, 89, 5517-5518. (b) Subsequent investigations presented convincing evidence that free radicals are involved under Ward's conditions: Ohnuki, T.; Yoshida, M.; Simamura, O. Chem. Lett. 1972, 999-1004.
34. (a) For a first report, see: Ward, H. R. J. Am. Chem. Soc. 1967, 89, 5517-5518. (b) Subsequent investigations presented convincing evidence that free radicals are involved under Ward's conditions: Ohnuki, T.; Yoshida, M.; Simamura, O. Chem. Lett. 1972, 999-1004.
35. (a) Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
36. (b) For an excellent review on the synthesis and reactions of N,N-dibenzylamino aldehydes, see: Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
37. (a) Ahrens, H. Dissertation, Universität Münster, 1994.
38. (b) Paetow, M.; Ahrens, H.; Hoppe, D. Tetrahedron Lett. 1992, 33, 5323-5326.
39. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769-3772.
40. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
41. The (E)-configuration of the double bond was assigned by a nuclear Overhauser effect of the vinylic proton and the proton at the carbon bearing the carbamate group.
42. (a) Oestreich, M. Dissertation, Universität Münster, 1999.
43. (b) Further functionalization of the alkylidene cyclopentanes in the vinylic position was representatively demonstrated for the stannylation of the intermediate vinylic lithium species.
44. Meyer, C.; Marek, I.; Normant, J. F.; Platzer, N. Tetrahedron Lett. 1994, 35, 5645-5648.
45. (a) Guarnieri, W.; Grehl, M.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1734-1737.
46. (b) Guarnieri, W.; Sendzik, M.; Fröhlich, R.; Hoppe, D. Synthesis 1998, 1274-1286.
47. (c) Sendzik, M.; Guarnieri, W.; Hoppe, D. Synthesis 1998, 1287-1297.
48. See also: (d) Gmeiner, P.; Junge, D.; Kärtner, A. J. Org. Chem. 1994, 59, 6766-6776.
49. For the Corey-Fuchs transformation of a-chiral aldehydes, see: Nicolaou, K. C.; Piscopio, A. D.; Bertinato, P.; Chakraborty, T. K.; Minowa, N.; Koide, K Chem. Eur. J. 1995, 1, 318-333.
50. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6191.
51. Hintze, F.; Hoppe, D. Synthesis 1992, 1216-1218.
52. For a representative procedure, see: Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384-1394.
53. The enantiomeric ratios were determined by Mosher ester analysis: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
54. Midland, M. M.; McLoughlin, J. I.; Gabriel, J. J. Org. Chem. 1984, 49, 1316-1317.
55. For a review, see: Midland, M. M. Chem. Rev. 1989, 89, 1553-1561.
56. Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 20, 95-98.
57. -3, Flack parameter 1.0(5), hydrogens calculated and riding (structure was already published in ref 7). See also ref 35.
58. For kinetic resolutions using the s-BuLi/1 reagent, see also: (a) Haller, J.; Hense, T.; Hoppe, D. Synlett 1993, 726-728. (b) Hense, T.; Hoppe, D. Synthesis 1997, 1394-1398.
59. For kinetic resolutions using the s-BuLi/1 reagent, see also: (a) Haller, J.; Hense, T.; Hoppe, D. Synlett 1993, 726-728. (b) Hense, T.; Hoppe, D. Synthesis 1997, 1394-1398.
60. See for example: Schwerdtfeger, J.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1992, 31, 1505-1507.
61. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
62. An dioxolane ring acting as a chelating group during carbamate lithiation has been described before: Helmke, H.; Hoppe, D. Synlett 1995, 978-980.
63. (a) Sakurai, H. Organosilicon and Bioorganosilicon Chemistry: Structure, Bonding, Reactivity, and Synthetic Applications; Halsted: New York, 1985.
64. (b) Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983.
65. 22 provided a 1:1 mixture of (S)-27 and its regioisomer. After a difficult separation of the regioisomers by flash chromatography (S)-27 was isolated in 29% yield.
66. -3, Flack parameter 0.01(2), disorder (51%:49%) around C15 (C14 and C151), hydrogens calculated and riding. The data set was collected with an Enraf Nonius CAD4 diffractometer. Programs used: data acquisation EXPRESS; data reduction MolEN; structure solution SHELXS-86; structure refinement SHELXL-93 and SHELXL-97; graphics DIAMOND.
67. For domino reactions, see: Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
68. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981.
69. The migration of a TBDPS group in a cis-1,3-cyclopentanediol system has already been observed: Torisawa, Y.; Shibasaki, M.; Ikegami, S. Chem. Pharm. Bull. 1983, 31, 2607-2615. We thank one of the reviewers for drawing our attention to this reference.
70. Another byproduct which was void of the trimethylsilyl group, compared to cis-34, was isolated in small quantities. The loss of the trimethylsilyl group may be due to the fact the lithium-oxygen bond in cis-32 is in the proximity of two silyl groups. A O to O-[1, 5]-shift regenerates the primary product cis-31, and a C to O-[1, 4]-shift of the trimethylsilyl group leads to the C-desilylated product after aqueous workup. For an example of such a migration, see eq 2 in: Lautens, M.; Delanghe, P. H. M.; Goh, J. B.; Zhang, C. H. J. Org. Chem. 1992, 57, 3270-3272.
71. For a comprehensive review on 1,3-allylic strain, see: Hoffmann. R. W. Chem. Rev. 1989, 89, 1841-1860.
72. (a) Lin, H.-S.; Paquette, L. A. Synth. Commun. 1994, 24, 2503-2506.
73. (b) Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1871-1880.
74. 3, 75.5 MHz) δ 205.3, 95.8, 93.9.