Efficient synthesis of α, β-diamino acid derivatives by in(III)-catalyzed regioselective addition of amines to aziridines

Synthetic Communications

Volumn 42, Issue 23, 2012, Pages 3403-3412

  Hu, Xiao Yu ^a,b   Yang, Xiang Yu ^a,b   Cheng, Ming ^a,b   Zhang, Qiang ^a,b   Wei, Wei ^a,b   Ji, Jian Xin ^a  

^a CHENGDU INSTITUTE OF BIOLOGY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

, diamino acid; Amines; aziridines; catalytic synthesis; indium(III) salt

Indexed keywords

AMINE; AMINO ACID DERIVATIVE; ANTIHYPERTENSIVE AGENT; AZIRIDINE DERIVATIVE; CARDIOVASCULAR AGENT; DIAMINO ACID; ETHYL 1 TOSYLAZIRIDINE 2 CARBOXYLATE; ETHYL 2 (3 BROMOPHENYLAMINO) 3 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 2 (4 FLUOROPHENYLAMINO) 3 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 2 (4 METHOXYPHENYLAMINO) 3 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 2 (4 METHYLPHENYLSULFONAMIDO) 3 (PHENYLAMINO)PROPANOATE; ETHYL 2 (4 METHYLPHENYLSULFONAMIDO) 3 MORPHOLINOPROPANOATE; ETHYL 2 (BENZYLAMINO) 3 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 2 (O TOLUIDINO) 3 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 2 (P TOLUIDINO) 3 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 3 (2,4 DIMETHOXYPHENYLAMINO) 2 (4 METHYLPHENYLSULFONAMIDO) PROPANOATE; ETHYL 3 (4 METHOXYPHENYLAMINO) 2 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; ETHYL 3 (4 METHYLPHENYLSULFONAMIDO) 2 (4 NITROPHENYLAMINO) PROPANOATE; ETHYL 3 (4 METHYLPHENYLSULFONAMIDO) 2 (PHENYLAMINO)PROPANOATE; ETHYL 3 (4 METHYLPHENYLSULFONAMIDO) 2 MORPHOLINOPROPANOATE; ETHYL 3 (P TOLUIDINO) 2 (4 METHYLPHENYLSULFONAMIDO)PROPANOATE; INDIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; RING OPENING; SYNTHESIS;

EID: 84864642682     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.582977     Document Type: Article

References (41)

1. (a) Hettinger, T. P.; Craig, L. C. Biochemistry 1970, 9, 1224-1232
2. (b) Astles, P. C.; Harris, N. V.; Morley, A. D. Bioorg. Med. Chem. 2001, 9, 2195-2202
3. (c) Wilczynski, A.; Wang, X. S.; Joseph, C. G.; Xiang, Z.; Bauzzo, R. M.; Scott, J. W.; Sorensen, N. B.; Shaw, A. M.; Millard, W. J.; Richards, N. G.; Haskell-Luevano, C. J. Med. Chem. 2004, 47, 2194-2207
4. (d) Batt, D. G.; Houghton, G. C.; Daneker, W. F.; Jadhav, P. K. J. Org. Chem. 2000, 65, 8100-8104.
5. (a) Tetsuji, K.; Tomohiro, O.; Hiroshi, H.; Masaki, O. Jpn. Kokai Tokkyo Koho, 2007, 2007112789
6. (b) Shota, I.; Manami, K.; Shuji, F. PCT Int. Appl., 2007, WO 2007034846.
7. Pessoa, J. C.; Marcão, S.; Correia, I.; Goncalves, G.; Dornyei, A.; Kiss, T.; Jakusch, T.; Tomaz, I.; Castro, M. M. C. A.; Geraldes, C. F. G. C.; Avecilla, F. Eur. J. Inorg. Chem. 2006, 3595-3606.
8. Viso, A.; Femadez de la Partilla, R.; Garcia, A.; Flores, A. Chem. Rev. 2005, 105, 3167-3196 and references cited hehein.
9. (a) Ojima, I.; Habus, I. Tetrahedron Lett. 1990, 31, 4289-4292
10. (b) van Maanen, H. L.; Kleijn, H.; Jastrzebski, J. T. B. H.; Verweij, J.; Kieboom, A. P. G.; van Koten, G. J. Org. Chem. 1995, 60, 4331-4338
11. (c) Brown, M. J.; Overman, L. E. J. Org. Chem. 1991, 56, 1933-1936
12. (d) DeMong, D. E.; Williams, R. M. J. Am. Chem. Soc. 2003, 125, 8561-8565
13. (e) Davis, F. A.; Deng, J. Org. Lett. 2005, 7, 621-623.
14. Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 35-42.
15. (a) You, S. L.; Kelly, J. W. Org. Lett. 2004, 6, 1681-1683
16. (b) Wenner, W. J. Org. Chem. 1948, 13, 26-30
17. (c) Verstappen, M. M. H.; Ariaans, G. J. A.; Zwanenburg, B. J. Am. Chem. Soc. 1996, 118, 8491-8492.
18. (a) Hu, X. E. Tetrahedron Lett. 2004, 60, 2701-2743
19. (b) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395-7398
20. (c) Yadav, J. S.; Reddy, B. V. S.; Jyothirmai, B.; Murty, M. S. R. Synlett 2002, 53-56
21. (d) Yavad, J. S.; Reddy, B. V. S.; Rao, K. V.; Raj, K. S.; Prasad, A. R. Synthesis 2002, 1061-1064
22. (e) Swamy, N. R.; Venkateswarlu, Y. Synth. Commun. 2003, 33, 547-554
23. (f) Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2003, 68, 5160-5167
24. (g) O'Neil, I. A.; Woolley, J. C.; Southern, J. M.; Hobbs, H. Tetrahedron Lett. 2001, 42, 8243-8245.
25. (a) Solomon, M. E.; Lynch, C. L.; Rich, D. H. Tetrahedron Lett. 1995, 36, 4955-4958
26. (b) Yamauchi, Y.; Kawate, T.; Katagiri, T.; Uneyama, K. Tetrahedron 2003, 59, 9839-9847
27. (c) Burgaud, B. G. M.; Horwell, D. C.; Padova, A.; Pritchard, M. C. Tetrahedron 1996, 52, 13035-13050
28. (d) Chakraborty, T. K.; Ghosh, A.; Raju, T. V. Chem. Lett. 2003, 32, 82-83
29. (e) Rinaudo, G.; Narizuka, S.; Askari, N.; Croussea, B.; Bonnet-Delpona, D. Tetrahedron Lett. 2006, 47, 2065-2068
30. (f) Crestey, F.; Witt, M.; Frydenvang, K.; Stærk, D.; Jaroszewski, J. W.; Franzyk, H. J. Org. Chem. 2008, 73, 3566-3569
31. (g) Antolini, L.; Bucciarelli, M.; Caselli, E.; Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. J. Org. Chem. 1997, 62, 8784-8789
32. (h) Kelley, B. T.; Joullié, M. M. Org. Lett. 2010, 12, 4244-4247
33. (i) Palomo, C.; Aizpurua, J. M.; Balentová, E.; Jimenez, A.; Oyarbide, J.; Fratila, R. M.; Miranda, J. I. Org. Lett. 2007, 9, 101-104
34. (j) Turner, J. J.; Sikkema, F. D.; Filippov, D. V.; van der Marel, G. A.; van Boom, J. H. Synlett 2001, 1727-1730
35. (k) 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.; Yun, H. Tetrahedron 2001, 57, 8267-8276
36. (l) Davoli, P.; Forni, A.; Moretti, I.; Prati, F. Tetrahedron: Asymmetry 1995, 6, 2011-2016
37. (m) Bucciarelli, M.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron: Asymmetry 1995, 6, 2073-2080
38. (n) Nadir, U. K.; Singh, A. Tetrahedron Lett. 2005, 46, 2083-2086
39. (o) Dauban, P.; Dodd, R. H. Tetrahedron Lett. 1998, 39, 5739-5742
40. (p) Kim, Y.; Ha, H.-J.; Han, K.; Ko, S. W.; Yun, H.; Yoon, H. J.; Kim, M. S.; Lee, W. K. Tetrahedron Lett. 2005, 46, 4407-4409.
41. Bongjin, M.; Sangbae, H.; Dohyung, K. Org. Lett. 2005, 7, 3359-3361.