Thermally induced and silver-salt-catalyzed [2+2] cycloadditions of imines to (Alkoxymethylene)cyclopropanes

Angewandte Chemie - International Edition

Volumn 45, Issue 31, 2006, Pages 5176-5179

  Nakamura, Itaru ^a   Nemoto, Tetsuya ^a   Yamamoto, Yoshinori ^a   De Armin, Meijere ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Amino acids; Cycloaddition; Cyclopropanes; Homogeneous catalysis; Silver

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; AROMATIC HYDROCARBONS; CATALYST ACTIVITY; REACTION KINETICS; SILVER;

CYCLOADDITION; CYCLOPROPANES; HOMOGENEOUS CATALYSIS;

NITROGEN COMPOUNDS;

EID: 33747275780     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600961     Document Type: Article

References (28)

1. For a review, see: S. France, A. Weatherwax, A. E. Taggi, T. Lectka, Acc. Chem. Res. 2004, 37, 592-600.
2. a) H. Staudinger, Justus Liebigs Ann. Chem. 1907, 356, 51-123;
3. for recent reports concerning the Staudinger reaction, see: b) C. Palomo, J. M. Aizpurua, I. Ganboa, M. Oiarbide, Eur. J. Org. Chem. 1999, 3223-3235;
4. c) S. France, H. Wack, A. M. Hafez, A. E. Taggi, D. R. Witsil, T. Lectka, Org. Lett. 2002, 4, 1603-1605;
5. d) B. L. Hodous, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 1578-1579;
6. e) A. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, T. Lectka, J. Am. Chem. Soc. 2002, 124, 6626-6635.
7. T. Akiyama, K. Daidouji, K. Fuchibe, Org. Lett. 2003, 5, 3691-3693.
8. J. A. Townes, M. A. Evans, J. Queffelec, S. J. Taylor, J. P. Morken, Org. Lett. 2002, 4, 2537-2540.
9. R. W. M. Aben, R. Smit, J. W. Scheeren, J. Org. Chem. 1987, 52, 365-370.
10. a) A. T. Bottini, L. J. Cabral, Tetrahedron 1978, 34, 3187-3194;
11. b) N. A. Petasis, E. I. Bzowej, Tetrahedron Lett. 1993, 34, 943-946.
12. A. de Meijere, A. Leonov, T. Heiner, M. Noltemeyer, M. T. Bes, Eur. J. Org. Chem. 2003, 3, 472-478.
13. CCDC-284945 (trans-3 ac) and CCDC-284946 (cis-3 ac) 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.
14. In a preliminary attempt to induce an asymmetric reaction of 1 a with 2 c with Ag(OTf) and (S)-binap as a chiral catalyst system, the product 3 ac was not obtained all.
15. a) H. Hart, J. M. Sandri, J. Am. Chem. Soc. 1959, 81, 320;
16. b) N. C. Deno, H. G. Richey, Jr., J. S. Liu, J. D. Hodge, J. J. Houser, M. J. Wisotsky, J. Am. Chem. Soc. 1962, 84, 2016;
17. c) D. D. Roberts, R. C. Snyder, Jr., J. Org. Chem. 1979, 44, 2860-2863;
18. d) For a review see: A. de Meijere, Angew. Chem. 1979, 91, 867-884;
19. Angew. Chem. Int. Ed. Engl. 1979, 18, 809-826.
20. B. H. Oh, I. Nakamura, S. Saito, Y. Yamamoto, Tetrahedron Lett. 2001, 42, 6203-6205.
21. M. Shi, B. Xu, J.-W. Huang, Org. Lett. 2004, 6, 1175-1178.
22. a) M. Shi, L.-X. Shao, B. Xu, Org. Lett. 2003, 5, 579-582;
23. b) L. Patient, M. B. Berry, S. J. Coles, M. B. Hursthouse, J. D. Kilburn, Chem. Commun. 2003, 2552-2553;
24. c) S. Rajamaki, J. D. Kilburn, Chem. Commun. 2005, 1637-1639.
25. Cf. D. L. Varie, C. Shih, D. A. Hay, S. L. Andis, T. H. Corbett, L. S. Gossett, S. K. Janisse, M. J. Martinelli, E. D. Moher, R. M. Schultz, J. E. Toth, Bioorg. Med. Chem. Lett. 1999, 9, 369-374.
26. a) D. Seebach, S. Abele, T. Sifferlen, M. Hänggi, S. Gruner, P. Seiler, Helv. Chim. Acta 1998, 81, 2218-2241;
27. b) S. Abele, P. Seiler, D. Seebach, Helv. Chim. Acta 1999, 82, 1559-1571;
28. c) S. Abele, D. Seebach, Eur. J. Org. Chem. 2000, 1-15.