Reagent-controlled diastereoselective synthesis of (2S,3R)- and (2R,3R)-2,3-diaminobutanoic acid derivatives using proline-catalyzed α-hydrazination reaction

Tetrahedron

Volumn 65, Issue 45, 2009, Pages 9468-9473

  Makino, Kazuishi ^a   Kubota, Sayaka ^a   Hara, Sousuke ^a   Sakaguchi, Masaru ^a   Hamajima, Akinari ^a   Hamada, Yasumasa ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Hydrazination; Alanine; Asymmetric synthesis; Diaminobutanoic acid; Organocatalyst; Proline

Indexed keywords

ALANINE; BUTYRIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 70349771927     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.064     Document Type: Article

References (35)

1. For a review, see:. Viso A., de la Pradilla R.F., Garcia A., and Flores A. Chem. Rev. 105 (2005) 3167-3196
2. Hara S., Makino K., and Hamada Y. Peptide Science 2005 (2006) p 39-42
3. Hara S., Makino K., and Hamada Y. Tetrahedron Lett. 47 (2006) 1081-1085
4. Hara S., Nagata E., Makino K., and Hamada Y. Peptide Science 2007 (2008) p 27-30
5. Makino K., Jiang H., Suzuki T., and Hamada Y. Tetrahedron: Asymmetry 17 (2006) 1644-1649
6. Makino K., Nagata E., and Hamada Y. Tetrahedron Lett. 46 (2005) 8159-8162
7. Makino K., Nagata E., and Hamada Y. Tetrahedron Lett. 46 (2005) 6827-6830
8. Dunn P.J., Haener R., and Rapoport H. J. Org. Chem. 55 (1990) 5017-5025
9. Schmidt U., Mundinger K., Riedl B., Haas G., and Lau R. Synthesis (1992) 1201-1202
10. Gonda J., Helland A.-C., Ernst B., and Bellus D. Synthesis (1993) 729-733
11. Nakamura Y., Hirai M., Tamotsu K., Yonezawa Y., and Shin C. Bull. Chem. Soc. Jpn. 68 (1995) 1369-1377
12. Merino P., Lanaspa A., Merchan F.L., and Tejero T. Tetrahedron Lett. 38 (1997) 1813-1816
13. Merino P., Lanaspa A., Merchan F.L., and Tejero T. Tetrahedron: Asymmetry 9 (1998) 629-646
14. Han H., Yoon J., and Janda K.D. J. Org. Chem. 63 (1998) 2045-2048
15. Kuwano R., Okuda S., and Ito Y. Tetrahedron: Asymmetry 9 (1998) 2773-2775
16. Knudsen K.R., Risgarrd T., Nishiwaki N., Gothelf K.V., and Jorgensen K.A. J. Am. Chem. Soc. 123 (2001) 5843-5844
17. Lee K.-D., Suh J.-M., Park J.-H., Ha H.-J., Choi H.G., Park C.S., Chang J.W., Lee W.K., Dong Y., and Yun H. Tetrahedron 57 (2001) 8267-8276
18. Dumez E., Szeki A., and Jackson R.F.W. Synthesis (2001) 1214-1216
19. Nishiwaki N., Kundsen K.R., Gothelf K.V., and Jorgensen K.A. Angew. Chem., Int. Ed. 40 (2001) 2992-2995
20. Robinson A.J., Stanislawski P., and Mulholland D. J. Org. Chem. 66 (2001) 4148-4152
21. Robinson A.J., and Lim C.Y. J. Org. Chem. 66 (2001) 4141-4147
22. Ambroise L., Dumez E., Szeki A., and Jackson R.F.W. Synthesis (2002) 2296-2308
23. Belllardi L., Gothelf A.S., Hazell R.G., and Jorgensen K.A. J. Org. Chem. 68 (2003) 2583-2591
24. Bunnage M.E., Burke A.J., Davis S.G., Millican N.L., Nicholson R.L., Roberts P.M., and Smith A.D. Org. Biomol. Chem. 1 (2003) 3708-3715
25. Ooi T., Kameda M., Fujii J., and Maruoka K. Org. Lett. 6 (2004) 2397-2399
26. Xie W., Ding D., Zi W., Li G., and Ma D. Angew. Chem., Int. Ed. 47 (2008) 2844-2848
27. Yoshitomi Y., Makino K., and Hamada Y. Org. Lett. 9 (2007) 2457-2460
28. Yoshitomi Y., Arai H., Makino K., and Hamada Y. Tetrahedron 64 (2008) 11568-11579
29. List B. J. Am. Chem. Soc. 124 (2002) 5656-5657
30. Bogevig A., Juhl K., Kumaragurubaran N., Zhuang W., and Jorgensen K.A. Angew. Chem., Int. Ed. 41 (2002) 1790-1793
31. Henmi Y., Makino K., Yoshitomi Y., Hara O., and Hamada Y. Tetrahedron: Asymmetry 15 (2004) 3477-3481
32. Caputo R., Cassano E., Longobardo L., and Palumbo G. Tetrahedron 51 (1995) 12337-12350
33. Etxebarria J., Vicario J.L., Badia D., and Carrillo L. Tetrahedron 63 (2007) 11421-11428
34. 3f This discrepancy was solved by HPLC analysis of the synthetic (2S,3R)-9, and its optical purity was unambiguously confirmed by the HPLC analysis of the synthetic (2R,3S)-9 and (2S,3R)-9. See Supplementary data.
35. 3f The optical purity of the synthetic (2R,3R)-9 was unambiguously confirmed by HPLC analysis of the synthetic (2R,3R)-9 and (2S,3S)-9. See Supplementary data.