Formation of 1-methylene-2-vinylcyclopropane by intramolecular S′E-cycloalkylation reaction

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6709-6711

  Brandau, Sven ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Carbamates; Cycloalkylation; Cyclopropanes

Indexed keywords

1 METHYLENE 2 VINYLCYCLOPROPANE; CARBAMIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 23944489817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.138     Document Type: Article

References (25)

1. T.C. Shields, W.E. Billups, and R.E. Lepley J. Am. Chem. Soc. 90 1968 4749 4751
2. A. Arora, and P. Binger Synthesis 1974 801 803
3. A.M. Brouwer, and H.J.C. Jacobs Recl. Trav. Chim. Pays-Bas 106 1987 48 53
4. A. de Meijere, S.I. Kozhushkov, D. Faber, V. Bagutskii, R. Boese, T. Haumann, and R. Walsh Eur. J. Org. Chem. 2001 3607 3614
5. P. Binger, A. Brinkmann, and P. Wedemann Synthesis 10 2002 1344 1346
6. W.E. Billups, T.C. Shields, W.Y. Chow, and N.C. Deno J. Org. Chem. 37 1972 3676 3678
7. Review: D. Hoppe, and T. Hense Angew. Chem. 109 1997 2376 2410
8. Angew. Chem., Int. Ed. 36 1997 2282 2316
9. M. Seppi, R. Kalkofen, J. Reupohl, R. Fröhlich, and D. Hoppe Angew. Chem. 116 2004 1447 1451
10. Angew. Chem., Int. Ed. 43 2004 1423 1427
11. Reviews: D. Hoppe, F. Marr, and M. Brüggemann D.M. Hodgson Organolithiums in Enantioselective Synthesis, Topics in Organometallic Chemistry Vol. 5 2003 Springer Berlin 61 138
12. G. Christoph, and D. Hoppe Asymmetric Deprotonation with Alkyllithium/(-)-Sparteine Z. Rappoport I. Marek The Chemistry of Organolithium Compounds. Part II 2004 Wiley Chichester 1058 1164
13. N. Mantlo, and S.J. Danishefsky J. Am. Chem. Soc. 110 1988 8129 8133
14. A.B. Smith, P.A. Levenberg, P.J. Jerris, R.M. Scarborough, and P.M. Wovkulich J. Am. Chem. Soc. 103 1981 1501 1513
15. T. Krämer, J.-R. Schwark, and D. Hoppe Tetrahedron Lett. 30 1989 7037 7040
16. D. Hoppe, and O. Zschage Angew. Chem. 101 1989 67 69
17. Angew. Chem., Int. Ed. Engl. 28 1989 69 71
18. D. Hoppe, and O. Zschage Tetrahedron 48 1992 5657 5666
19. T. Krämer, and D. Hoppe Tetrahedron Lett. 28 1987 5149 5152
20. H. Bosshardt, and M. Schlosser Helv. Chim. Acta 23 1980 2393 2403
21. M. Schlosser Angew. Chem. 86 1974 751 788
22. Angew. Chem., Int. Ed. Engl. 13 1974 701 706
23. -3, hydrogens calculated and refined as riding atoms. Data set was collected with a Nonius KappaCCD diffractometer. Programs used: data collection COLLECT (Nonius B. V., 1998), data reduction Denzo-SMN (Otwinowski, Z., Minor, W. Methods in Enzymology, 1997, 276, 307-326), absorption correction Denzo (Otwinowski, Z., Borek, D., Majewski, W., Minor, W. Acta Cryst. 2003, A59, 228-234), structure solution shelxs-97 (Sheldrick, G. M. Acta Cryst. 1990, A46, 467-473), structure refinement shelxl-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E., 1997). Crystallographic data (excluding structure factors) for the structure of 8 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 260661. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
24. 1H NMR spectra. The absolute configuration of 8 remains unclear.
25. 3) at 50% ee (er = 75:25).