Reaction of magnesium cyclopropylidene with N-lithio arylamines: a method for generation of α-amino-substituted cyclopropylmagnesiums and a study for their reactivity with electrophiles

Tetrahedron

Volumn 62, Issue 17, 2006, Pages 4253-4261

  Satoh, Tsuyoshi ^a   Miura, Mariko ^a   Sakai, Ken ^b   Yokoyama, Yoshimi ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

Amino substituted cyclopropylmagnesium; Cyclopropane amino acid; Magnesium cyclopropylidene; Sulfoxide; Sulfoxide magnesium exchange

Indexed keywords

1 CHLOROCYCLOPROPYLPHENYL SULFOXIDE; AMINO ACID DERIVATIVE; AROMATIC AMINE; MAGNESIUM CHLORIDE; MAGNESIUM CYCLOPROPYLIDENE; MAGNESIUM DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE;

EID: 33645965855     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.080     Document Type: Article

References (44)

1. Some monographs and reviews concerning carbenes and carbenoids: (a). Kirmse W. Carbene Chemistry (1971), Academic, New York
2. Dorwald F.Z. Metal Carbenes in Organic Synthesis (1999), Wiley-VCH, Weinheim
3. In: Bertrand G. (Ed). Carbene Chemistry (2002), Marcel Dekker, New York
4. Kobrich G. Angew. Chem., Int. Ed. Engl. 11 (1972) 473
5. Stang P.J. Chem. Rev. 78 (1978) 383
6. Burke S.D., and Grieco P.A. Org. React. 26 (1979) 361
7. Schaefer III H.F. Acc. Chem. Res. 12 (1979) 288
8. Wynberg H., and Meijer E.W. Org. React. 28 (1982) 1
9. Oku A., and Harada T. J. Synth. Org. Chem. Jpn. 44 (1986) 736
10. Oku A. J. Synth. Org. Chem. Jpn. 48 (1990) 710
11. Padwa A., and Krumpe K.E. Tetrahedron 48 (1992) 5385
12. Padwa A., and Weingarten M.D. Chem. Rev. 96 (1996) 223
13. Braun M. Angew. Chem., Int. Ed. 37 (1998) 430
14. Brandsma L., and Verkruijsse H.D. Synthesis of Acetylenes, Allenes and Cumulenes (1981), Elsevier Scientific, Amsterdam
15. Schuster H.F., and Coppola G.M. Allenes in Organic Synthesis (1984), Wiley, New York
16. Some monographs and papers: (a). Hassner A., and Stumer C. Organic Syntheses Based on Name Reactions and Unnamed Reactions (1994), Elsevier, Oxford
17. Li J.J. Name Reactions (2002), Springer, Berlin
18. Doering W.v.E., and LaFlamme P.M. Tetrahedron 2 (1958) 75
19. Moore W.R., and Ward H.R. J. Org. Chem. 25 (1960) 2073
20. Skattebol L. Tetrahedron Lett. (1961) 167
21. Moore W.R., and Ward H.R. J. Org. Chem. 27 (1962) 4179
22. Satoh T., and Takano K. Tetrahedron 52 (1996) 2349
23. Satoh T., Kondo A., and Musashi J. Tetrahedron 60 (2004) 5453
24. Satoh T., Osawa A., and Kondo A. Tetrahedron Lett. 45 (2004) 6703
25. Satoh T., Musashi J., and Kondo A. Tetrahedron Lett. 46 (2005) 599
26. Miyashita K., and Satoh T. Tetrahedron 61 (2005) 5067
27. Satoh T., Takano K., Ota H., Someya H., Matsuda K., and Koyama M. Tetrahedron 54 (1998) 5557
28. Satoh T., Sakamoto T., and Watanabe M. Tetrahedron Lett. 43 (2002) 2043
29. Satoh T., Ogino Y., and Nakamura M. Tetrahedron Lett. 45 (2004) 5785
30. Watanabe M., Nakamura M., and Satoh T. Tetrahedron 61 (2005) 4409
31. Satoh T., Sakurada J., and Ogino Y. Tetrahedron Lett. 46 (2005) 4855
32. Satoh T. J. Synth. Org. Chem. Jpn. 54 (1996) 481
33. Satoh T. J. Synth. Org. Chem. Jpn. 61 (2003) 98
34. Satoh T. The Chemical Record 3 (2004) 329
35. Satoh T., Kurihara T., and Fujita K. Tetrahedron 57 (2001) 5369
36. Satoh T., and Saito S. Tetrahedron Lett. 45 (2004) 347
37. Kirihara M., Kawasaki M., Takuwa T., Kakuwa T., Kakuda H., Wakikawa T., Takeuchi Y., and Kirk K.L. Tetrahedron: Asymmetry 14 (2003) 1753
38. Adams L.A., Aggarwal V.K., Bonnert R.V., Bressel B., Cox R.J., Shepherd J., de Vincente J., Walter M., Whittingham W.G., and Winn C.L. J. Org. Chem. 68 (2003) 9433
39. Allwein S.P., Secord E.A., Martins A., Mitten J.V., Nelson T.D., Kress M.H., and Dolling U.H. Synlett (2004) 2489
40. Wurz R.P., and Charette A.B. J. Org. Chem. 69 (2004) 1262 and the references cited therein
41. Cazes B., and Julia S. Tetrahedron Lett. (1978) 4065
42. Metzner P., and Thuillier A. Sulfur Reagents in Organic Synthesis (1994), Academic, London
43. Berrada S., Desert S., and Metzner P. Tetrahedron 44 (1988) 3575
44. α radiation. The data reduction, structure solution and refinement, and all the necessary computational data processes were performed using SMART, SAINT, SHELXTL, KENX, and TEXSAN programs. Data deposited at the Cambridge Crystallographic Data Centre; deposition number CCDC 285997.