Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

Tetrahedron Letters

Volumn 48, Issue 36, 2007, Pages 6304-6307

  Nemoto, Tetsuhiro ^a   Harada, Teisuke ^a   Matsumoto, Takayoshi ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Asymmetric allylic alkylation; Diaminophosphine oxides; Palladium; Quaternary amino acids

Indexed keywords

ALPHA AMINO ACID; BETA KETO ESTER; CARBON; DIAMINOPHOSPHINE OXIDE; ESTER; PALLADIUM; PHENYLALANINE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; SYNTHESIS;

EID: 34547673716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.020     Document Type: Article

References (56)

1. For reviews on peptidomimetic chemistry, see:. Giannis A., and Kolter T. Angew. Chem., Int. Ed. Engl. 32 (1993) 1244
2. Gante J. Angew. Chem., Int. Ed. Engl. 33 (1994) 1699
3. Hanessian S., McNaughton-Smith G., Lombart H.G., and Lubell W.D. Tetrahedron 53 (1997) 12789
4. For reviews on asymmetric synthesis of quaternary α-amino acid derivatives, see:. Cativiela C., and Díaz-de-Villegas M.D. Tetrahedron: Asymmetry 9 (1998) 3517
5. Cativiela C., and Díaz-de-Villegas M.D. Tetrahedron: Asymmetry 11 (2000) 645
6. Park K.-H., and Kurth M.J. Tetrahedron 58 (2002) 8629
7. Gröger H. Chem. Rev. 103 (2003) 2795
8. For recent leading references of catalytic asymmetric synthesis of quaternary α-amino acid derivatives, see:. Funabashi K., Ratni H., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 123 (2001) 10784
9. Vachal P., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 10012
10. Masumoto S., Usuda H., Suzuki M., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 5634
11. Sabby S., Bella M., and Jørgensen K.A. J. Am. Chem. Soc. 126 (2004) 8120
12. Zhuang W., Saaby S., and Jørgensen K.A. Angew. Chem., Int. Ed. 43 (2004) 4476
13. Belokon Y.N., Bhave D., D'Addario D., Groaz E., North M., and Tagliazucca V. Tetrahedron 60 (2004) 1849
14. Kitamura M., Shirakawa S., and Maruoka K. Angew. Chem., Int. Ed. 44 (2005) 1549
15. Liu X., Li H., and Deng L. Org. Lett. 7 (2005) 167
16. Ooi T., Miki T., and Maruoka K. Org. Lett. 7 (2005) 191
17. Suri J.T., Steiner D.D., and Barbas III C.F. Org. Lett. 7 (2005) 3885
18. Balskus E.P., and Jacobsen E.N. J. Am. Chem. Soc. 128 (2006) 6810
19. Fustero S., Sánchez-Roselló M., Rodrigo V., del Pozo C., Sanz-Cervera J.F., and Simón A. Org. Lett. 8 (2006) 4129
20. For asymmetric synthesis of quaternary α-amino acid derivatives via memory of chirality, see:. Kawabata T., Kawakami S., and Majumdar S. J. Am. Chem. Soc. 125 (2003) 13012
21. Kawabata T., Matsuda S., Kawakami S., Monguchi D., and Moriyama K. J. Am. Chem. Soc. 128 (2006) 15394
22. For representative examples of enantioselective construction of a quaternary carbon through Pd-catalyzed asymmetric allylic substitution, see:. Hayashi T., Kanehira K., Tsuchiya H., and Kumada M. J. Chem. Soc., Chem. Commun. (1982) 116
23. Sawamura M., Nagata H., Sakamoto H., and Ito Y. J. Am. Chem. Soc. 114 (1992) 2586
24. Sawamura M., Sudoh M., and Ito Y. J. Am. Chem. Soc. 118 (1996) 3309
25. Trost B.M., Radinov R., and Grenzer E.M. J. Am. Chem. Soc. 119 (1997) 7879
26. Trost B.M., and Schroeder G.M. J. Am. Chem. Soc. 121 (1999) 6759
27. You S.-L., Hou X.-L., Dai L.-X., and Zhu X.-Z. Org. Lett. 3 (2001) 149
28. Nakoji M., Kaneyama T., Okino T., and Takemoto Y. J. Org. Chem. 67 (2002) 7418
29. Kuwano R., Uchida K., and Ito Y. Org. Lett. 5 (2003) 2177
30. Behenna D.C., and Stoltz B.M. J. Am. Chem. Soc. 126 (2004) 15044
31. Trost B.M., and Frederiksen M.U. Angew. Chem., Int. Ed. 44 (2005) 308
32. Trost B.M., and Xu J. J. Am. Chem. Soc. 127 (2005) 2846
33. Mohr J.T., Behenna D.C., Harned A.M., and Stoltz B.M. Angew. Chem., Int. Ed. 44 (2005) 6924
34. Trost B.M., Bream R.N., and Xu J. Angew. Chem., Int. Ed. 45 (2006) 3109
35. For a review, see:. Trost B.M., and Jiang C. Synthesis (2006) 369
36. Kuwano R., and Ito Y. J. Am. Chem. Soc. 121 (1999) 3236
37. Ogasawara M., Ngo H.L., Sakamoto T., Takahashi T., and Lin W. Org. Lett. 7 (2005) 2881
38. α-Acetamido β-keto phosphonates as the nucleophiles, see:. Kuwano R., Nishio R., and Ito Y. Org. Lett. 1 (1999) 837
39. Azlactones are also useful nucleophiles for providing access to chiral quaternary α-amino acid derivatives, see:. Trost B.M., and Ariza X. Angew. Chem., Int. Ed. 36 (1997) 2635
40. Trost B.M., and Ariza X. J. Am. Chem. Soc. 121 (1999) 10727
41. Trost B.M., and Dogra K. J. Am. Chem. Soc. 124 (2002) 7256
42. Nemoto T., Matsumoto T., Masuda T., Hitomi T., Hatano K., and Hamada Y. J. Am. Chem. Soc. 126 (2004) 3690
43. Nemoto T., Masuda T., Matsumoto T., and Hamada Y. J. Org. Chem. 70 (2005) 7172
44. Nemoto T., Fukuda T., Matsumoto T., Hitomi T., and Hamada Y. Adv. Synth. Catal. 347 (2005) 1504
45. Nemoto T., Masuda T., Akimoto Y., Fukuyama T., and Hamada Y. Org. Lett. 7 (2005) 4447
46. Nemoto T., Jin L., Nakamura H., and Hamada Y. Tetrahedron Lett. 47 (2006) 6577
47. Nemoto T., Sakamoto T., Matsumoto T., and Hamada Y. Tetrahedron Lett. 47 (2006) 8737
48. Nemoto T., Fukuyama T., Yamamoto E., Tamura S., Fukuda T., Matsumoto T., Akimoto Y., and Hamada Y. Org. Lett. 9 (2007) 927
49. Nemoto T., Sakamoto T., Fukuyama T., and Hamada Y. Tetrahedron Lett. 48 (2007) 4977
50. For reviews on phosphine oxide preligands in transition metal catalysis, see:. Dubrovina N.V., and Börner A. Angew. Chem., Int. Ed. 43 (2004) 5883
51. Ackermann L. Synthesis (2006) 1557
52. Ackermann L. Synlett (2007) 507
53. Nemoto T., and Hamada Y. Chem. Rec. 7 (2007) 150
54. See Supplementary data for details.
55. For the general procedure, see Supplementary data.
56. Although the role of additives in the present catalytic asymmetric reaction is unknown, NMR experiments indicated that KOAc might be related to the generation of active nucleophiles. For experimental data, see Supplementary data.