Enantioselective synthesis of functionalized 1,5-cyclononadienes by intramolecular cycloalkylation under α,α'-diallyl coupling

Angewandte Chemie - International Edition

Volumn 39, Issue 12, 2000, Pages 2105-2107

  Deiters, Alexander ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Carbanions; Cyclizations; Lithium; Medium sized rings; Sparteine

Indexed keywords

ALKADIENE; CARBAMIC ACID DERIVATIVE; LITHIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CRYSTAL STRUCTURE; ENANTIOMER; ISOMERISM; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0040778612     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000616)39:12<2105::AID-ANIE2105>3.0.CO;2-X     Document Type: Article

References (47)

1. The synthesis of nine-membered rings is particularly strongly disfavored because of the adverse entropic term, the Baeyer strain, and the Pitzer strain, as well as the transannular interactions: E. L. Eliel, S. H. Wilen in Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 675-685.
2. a) A. T. Bloomquist, Y. C. Meinwald, J. Am. Chem. Soc. 1958, 80, 630-632;
3. b) T. Lecta in Active Metals (Ed.: A. Fürstner), VCH, Weinheim, 1995, pp. 85-132; J.E. McMurry, K. L. Kees, J. Org. Chem. 1977, 42, 2655-2656;
4. b) T. Lecta in Active Metals (Ed.: A. Fürstner), VCH, Weinheim, 1995, pp. 85-132; J.E. McMurry, K. L. Kees, J. Org. Chem. 1977, 42, 2655-2656;
5. c) Other ring-closing reactions leading to monocarbocyclic nine-membered rings; intramolecular 1,4-addition (35% yield): P. Deslongchamps, B. L. Roy, Can. J. Chem. 1986, 64, 2068-2075;
6. Thorpe-Ziegler condensation (3% yield): J. P. Schaefer, J. J. Bloomfield, Org. React. 1967, 15, 3-203.
7. A. Deiters, D. Hoppe, Angew. Chem. 1999, 111, 529-532; Angew. Chem. Int. Ed. 1999, 38, 546-548.
8. A. Deiters, D. Hoppe, Angew. Chem. 1999, 111, 529-532; Angew. Chem. Int. Ed. 1999, 38, 546-548.
9. P. Lennon, M. Rosenblum, J. Am. Chem. Soc. 1983, 105, 1233-1241.
10. Reviews: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
11. Reviews: a) D. Hoppe, T. Hense, Angew. Chem. 1997, 109, 2376-2410; Angew. Chem. Int. Ed. Engl. 1997, 36, 2282-2316;
12. b) P. Beak, A. Basu, D. J. Gallagher, Y. S. Park, S. Thayumanavan, Acc. Chem. Res. 1996. 29, 552-560.
13. 2O at -78 C, rac-4 is yielded in 76%.
14. 3J=10.1, 8.5 Hz), The enantiomeric ratio of 4 was determined by gas chromatography on a chiral stationary phase (Beta-Dex 120, Supelco, USA).
15. [5a] A correlation of the optical rotations assigned the R configuration for (+)-5.
16. Stereoinversion in the silylation of allyllithium-(-)-sparteine complexes: K. Behrens, R. Fröhlich, O. Meyer, D. Hoppe, Eur. J. Org. Chem. 1998, 2397-2403: H. Paulsen, C. Graeve, D. Hoppe, Synthesis 1996, 141-144.
17. Stereoinversion in the silylation of allyllithium-(-)-sparteine complexes: K. Behrens, R. Fröhlich, O. Meyer, D. Hoppe, Eur. J. Org. Chem. 1998, 2397-2403: H. Paulsen, C. Graeve, D. Hoppe, Synthesis 1996, 141-144.
18. [10b] However, an intramolecular coupling reaction was unknown: A. Yanagisawa, K. Yasue, H. Yamamoto, Synlett 1996, 842-844: A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, H. Yamamoto, J. Org. Chem. 1992, 57, 6386-6387;
19. [10b] However, an intramolecular coupling reaction was unknown: A. Yanagisawa, K. Yasue, H. Yamamoto, Synlett 1996, 842-844: A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, H. Yamamoto, J. Org. Chem. 1992, 57, 6386-6387;
20. b) A. Yanagisawa, H. Yamamoto in Active Metals (Ed.: A. Fürstner), VCH, Weinheim, 1995, pp. 61-84.
21. Presumably, the topology of the transition state A is influenced by π-π* interactions of the allylic moieties by precoordination and, therefore, favor the entropic term of the cyclization. In principle a γ,γ′-coupling between C-3 and C-7 is also possible and would lead to the cis configured five-membered ring. However, this would cause an increase of transannular and diaxial interactions of the side chains with the ring system: for this reason, the formation of a nine-membered ring takes place.
22. F. Hintze, D. Hoppe, Synthesis 1992, 1216-1218.
23. [16b]
24. a) For 2-alkynyl carbamates, see: S. Dreller, M. Dyrbusch, D. Hoppe, Synlett 1991, 397-400;
25. b) For a similar reaction sequence, see: S. Hatakeyama, H. Irie, T. Shintani, Y. Noguchi, H. Yamada, M. Nishizawa, Tetrahedron 1994, 50, 13 369-13 376.
26. 3J=10.6, 5.7 Hz), 5.67-5.81 (m, 3H, CH, CH, CH), 7.32-7.70 (m, 10H, CH(phenyl)). After cleavage of the TBDPS group, the enantiomeric ratio of (1R,5S)-10 was determined as described in reference [7].
27. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
28. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
29. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
30. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
31. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
32. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
33. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
34. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
35. 3, Flack Parameter 0.3(2), the asymmetric unit contains two independent, nearly identical molecules, hydrogens were calculated and refined as riding atoms: b) The data sets were collected with Nonius CAD4 and Nonius KappaCCD diffractometers equipped with a Nonius FR590 sealed tube generator or a Nonius FR591 rotating anode generator. The following programs were used: For data collection, EXPRESS (Nonius B.V., 1994) and COLLECT (Nonius B.V., 1998); for data reduction, MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN (Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326); for absorption corrections for CCD data, SORTAV (R. H. Blessing, Acta Crystallogr. Sect. A 1995, 51, 33-37; R. H. Blessing, J. Appl. Crystallogr. 1997, 30, 421-426); for structure solution, SHELXS-97 (G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473); for structure refinement, SHELXL-97 (G. M. Sheldrick, University of Göttingen. 1997); for graphics, SCHAKAL (E. Keller, University of Freiburg, 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139019 and -139020. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
36. [22] Cope rearrangement of (Z,Z)-cyclonona-1,5-diene: E. Vogel, W. Grimme, E. Dinné, Angew. Chem. 1963, 75, 1103.
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38. b) anionic oxy-Cope rearrangement of rac-6: L. A. Paquette, G. D. Crouse, A. K. Sharma, J. Am. Chem. Soc. 1982, 104, 4411-4423. The enantiomeric ratio of 13 was determined as described in reference [7].
39. a) S.-Y. Wei, K. Tomooka, T. Nakai, Tetrahedron 1993, 49, 1025-1042;
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41. b) L. A. Paquette, G. D. Maynard, Angew. Chem. 1991, 103, 1392-1394; Angew. Chem. Int. Ed. Eng. 1991, 30, 1368-1370:
42. c) in anionic oxy-Cope rearrangements the oxido group prefers an equatorial position: L. A. Paquette, G. Maynard, J. Am. Chem. Soc. 1992, 114, 5018-5027.
43. K. Tomooka, N. Komine, T. Sasaki, H. Shimizu, T. Nakai, Tetrahedron Lett. 1998, 39, 9715-9718.
44. Review of homoenolate chemistry: D. Hoppe, Angew. Chem. 1984, 96, 930-946; Angew. Chem. Int. Ed. Engl, 1984, 23, 932-948.
45. Review of homoenolate chemistry: D. Hoppe, Angew. Chem. 1984, 96, 930-946; Angew. Chem. Int. Ed. Engl, 1984, 23, 932-948.
46. A. Deiters, D. Hoppe, unpublished results.
47. All new compounds were analytically pure (error in C,H,N elemental analyses ±0.4).