Enantioselective synthesis of α,α-disubstituted α-amino acids by Rh-catalyzed [2+2+2] cycloaddition of 1,6-diynes with protected dehydroamino acid

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6289-6293

  Tanaka, Ken ^a   Takahashi, Maho ^a   Imase, Hidetomo ^a   Osaka, Takuya ^a   Noguchi, Keiichi ^a   Hirano, Masao ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 DIYNE DERIVATIVE; ALKYNE DERIVATIVE; ALPHA AMINO ACID; ALPHA,ALPHAN,ALPHA AMINO ACID DERIVATIVE; DEHYDROAMINO ACID; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 44349186060     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.107     Document Type: Article

References (51)

1. Chi Y., Tang W., and Zhang X. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim Chapter 1, pp 1-31
2. Halpern J. In: Morrison J.D. (Ed). Asymmetric Catalytic Hydrogenation: Mechanism and Origin of Enantioselection in Asymmetric Synthesis Vol. 5 (1985), Academic, Orlando, FL 41-69
3. Gridnev l.D., Imamoto T., Hoge G., Kouchi M., and Takahashi H. J. Am. Chem. Soc. 130 (2008) 2560-2572
4. For examples, see:
5. Tanaka M. Chem. Pharm. Bull. 55 (2007) 349-358
6. Bellier B., McCort-Tranchenpain I., Ducos B., Danascimento S., Meudal H., Noble F., Garbay C., and Roques B.P. J. Med. Chem. 40 (1997) 3947-3956
7. Mossel E., Formaggio F., Crisma M., Toniolo C., Broxterman Q.B., Boesten W.H.J., Kamphuis J., Quaedflieg P.J.L.M., and Temussi P. Tetrahedron: Asymmetry 8 (1997) 1305-1314
8. Dery O., Josien H., Grassi J., Chassaing G., Couraud J.Y., and Lavielle S. Biopolymers 39 (1996) 67-74
9. Benedetti E., Gavuzzo E., Santini A., Kent D.R., Zhu Y.-F., Zhu Q., Mahr C., and Goodman M. J. Pept. Sci. 1 (1995) 349-359
10. For reviews of asymmetric synthesis of α,α-disubstituted α-amino acids, see:
11. Vogt H., and Braese S. Org. Biomol. Chem. 5 (2007) 406-430
12. Ohfune Y., and Shinada T. Eur. J. Org. Chem. (2005) 5127-5143
13. Park K.H., and Kurth M.J. Tetrahedron 58 (2002) 8629-8659
14. Cativiela C., and Diaz-de-Villegas M.D. Tetrahedron: Asymmetry 11 (2000) 645-732
15. Gibson S.E., Guillo N., and Tozer M.J. Tetrahedron 55 (1999) 585-615
16. Cativiela C., and Diaz-de-Villegas M.D. Tetrahedron: Asymmetry 9 (1998) 3517-3599
17. Wirth T. Angew. Chem., Int. Ed. 36 (1997) 225-227
18. Seebach D., Sting A.R., and Hoffmann M. Angew. Chem., Int. Ed. 35 (1996) 2708-2748
19. Synthesis of unusual α,α-disubstituted α-amino acids by transition metal-catalyzed [2+2+2] cycloadditions, see:. Kotha S. Acc. Chem. Res. 36 (2003) 342-351
20. For recent reviews of transition metal-catalyzed [2+2+2] cycloadditions, see:
21. Agenet N., Buisine O., Slowinski F., Gandon V., Aubert C., and Malacria M. In: Overman L.E. (Ed). Organic Reactions Vol. 68 (2007), John Wiley & Sons, Hoboken, NJ pp 1-302
22. Chopade P.R., and Louie J. Adv. Synth. Catal. 348 (2006) 2307-2327
23. Gandon V., Aubert C., and Malacria M. Chem. Commun. (2006) 2209-2217
24. Kotha S., Brahmachary E., and Lahiri K. Eur. J. Org. Chem. (2005) 4741-4767
25. Yamamoto Y. Curr. Org. Chem. 9 (2005) 503-509
26. Fujiwara M., and Ojima I. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim Chapter 7, pp 129-149
27. For our first discovery of a cationic rhodium(I)/modified-BINAP complex as a catalyst for [2+2+2] cycloadditions, see:
28. Tanaka K., and Shirasaka K. Org. Lett. 5 (2003) 4697-4699
29. Tanaka K., Toyoda K., Wada A., Shirasaka K., and Hirano M. Chem.-Eur. J. 11 (2005) 1145-1156
30. For our accounts, see:
31. Tanaka K. Synlett (2007) 1977-1993
32. Tanaka K., Nishida G., and Suda T. J. Synth. Org. Chem. Jpn. 65 (2007) 862-873
33. Tsuchikama K., Kuwata Y., and Shibata T. J. Am. Chem. Soc. 128 (2006) 13686-13687
34. Tanaka K., Nishida G., Sagae H., and Hirano M. Synlett (2007) 1426-1430
35. Shibata T., Kawachi A., Ogawa M., Kuwata Y., Tsuchikama K., and Endo K. Tetrahedron 63 (2007) 12853-12859
36. For a Ni-catalyzed enantioselective [2+2+2] cycloaddition of monoalkynes with monoalkenes, see:. Ikeda S., Kondo H., Arii T., and Odashima K. Chem. Commun. (2002) 2422-2423
37. Co-mediated [2+2+2] cycloadditions of alkynes with double bonds in nitrogen heterocycles, see:
38. Aubert C., Betschmann P., Eichberg M.J., Gandon V., Heckrodt T.J., Lehmann J., Malacria M., Masjost B., Paredes E., Vollhardt K.P.C., and Whitener G.D. Chem.-Eur. J. 13 (2007) 7443-7465
39. Pellissier H., Rodriguez J., and Vollhardt K.P.C. Chem.-Eur. J. 5 (1999) 3549-3561
40. Boese R., Van Sickle A.P., and Vollhardt K.P.C. Synthesis (1994) 1374-1382
41. Boese R., Rodriguez J., and Vollhardt K.P.C. Angew. Chem., Int. Ed. Engl. 30 (1991) 993-994
42. Boese R., Knölker H.-J., and Vollhardt K.P.C. Angew. Chem., Int. Ed. Engl. 26 (1987) 1035-1037
43. Sheppard G.S., and Vollhardt K.P.C. J. Org. Chem. 51 (1986) 5496-5498
44. Grotjahn D.B., and Vollhardt K.P.C. J. Am. Chem. Soc. 108 (1986) 2091-2093
45. Ru-catalyzed linear cooligomerization of enamides with alkenes or alkynes, see:. Tsujita H., Ura Y., Matsuki S., Wada K., Mitsudo T., and Kondo T. Angew. Chem., Int. Ed. 46 (2007) 5160-5163
46. Nishida G., Noguchi K., Hinano M., and Tanaka K. Angew. Chem., Int. Ed. 46 (2007) 3951-3954
47. Tanaka K., Wada A., and Noguchi K. Org. Lett. 8 (2006) 907-909
48. Kudoh T., Mori T., Shirahama M., Yamada M., Ishikawa T., Saito S., and Kobayashi H. J. Am. Chem. Soc. 129 (2007) 4939-4947
49. Tanaka K., Takeishi K., and Noguchi K. J. Am. Chem. Soc. 128 (2006) 4586-4587
50. Hosokawa T., Takano M., Kuroki Y., and Murahashi S. Tetrahedron Lett. 33 (1992) 6643-6646
51. Azizian J., Hatamjafari F., Karimi A.R., and Shaabanzadeh M. Synthesis (2006) 765-767