An organocatalyzed enantioselective synthesis of (2S,3R,4S)-4- hydroxyisoleucine and its stereoisomers

Journal of Organic Chemistry

Volumn 75, Issue 8, 2010, Pages 2745-2747

  Kumaraswamy, Gullapalli ^a   Jayaprakash, Neerasa ^a   Sridhar, Balasubramanian ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; KEY FEATURE; MANNICH REACTIONS;

STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

4 HYDROXYISOLEUCINE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; ISOLEUCINE; KINETICS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 77951010289     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100233u     Document Type: Article

References (27)

1. Sauvaire, Y.; Petit, P.; Broca, C.; Manteghetti, M.; Baissac, Y.; Fernandez-Alavarez, J.; Gross, R.; Roye, M.; Leconte, A.; Gomis, R.; Ribes, G. Diabetes 1998, 47, 206
2. Narender, T.; Puri, A.; Shweta; Khaliq, T.; Saxena, R.; Bhatia, G.; Chandra, R. Bioorg. Med. Chem. Lett. 2006, 16, 293
3. Fowden, L.; Pratt, H. M.; Smith, A. Phytochemistry 1973, 12, 1707
4. Alcock, N. W.; Crout, D. H. G.; Gregorio, M. V. M.; Lee, E.; Pike, G.; Samuel, C. J. Phytochemistry 1989, 20, 1835
5. Broca, C.; Manteghetti, M.; Gross, R.; Baissac, Y.; Jacob, M.; Petit, P.; Sauvaire, Y.; Ribes, G. Eur. J. Pharmacol. 2000, 390, 339
6. Raffauf, R. F.; Zennie, T. M.; Onan, K. D.; Le Quesne, P. W. J. Org. Chem. 1984, 49, 2714
7. Kassem, T.; Wehbe, J.; Rolland-Fulcrand, V.; Rolland, M.; Roumestant, M. L.; Martinez, J. Tetrahedron: Asymmetry 2001, 12, 2657
8. Gull, R.; Schollkopf, U. Synthesis 1985, 1052
9. Inghardt, T.; Frejd, T.; Svensson, G. Tetrahedron 1991, 47, 6469
10. Jamieson, A. G.; Sutherland, A.; Willis, C. L. Org. Biomol. Chem. 2004, 2, 808-809
11. Sergent, D.; wang, Q.; Sasaki, N. A.; Ouazzani, J. Bioorg. Med. Chem. Lett. 2008, 18, 4332-4335
12. Wang, Q.; Ouazzani, J.; Sasaki, N. A.; Potier, P. Eur. J. Org. Chem. 2002, 834
13. Ibrahem, I.; Cordova, A. Chem. Commun 2006, 1760
14. Trost, B. M.; Jaratjaroong, J. J. Am. Chem. Soc. 2006, 128, 2778
15. Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 16408
16. Mitsumori, S.; Zhang, H.; Cheong, P. H.-Y.; Houk, K. N.; Tanaka, F.; Barbas, C. F., III J. Am. Chem. Soc. 2006, 128, 1040
17. Gianelli, C.; Sambri, L.; Carlone, A.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8700-8702
18. Yang, J. W.; Stadler, M.; List, B. Angew. Chem. Int. Ed 2007, 46, 609
19. Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed 2003, 42, 3677
20. Fustero, S.; Jimenez, D.; Sanz-Cervera, J. F.; Sanchez-Rosello, M.; Esteban, E.; Simon-Fuentes, A. Org. Lett. 2005, 7, 3433
21. Cardova, A.; Barbas, C. F., III Tetrahedron Lett. 2002, 43, 7749
22. Liao, W. W.; Ibrahem, I.; Cardova, A. Chem. Commun. 2006, 674
23. Enders, D.; Grondal, C.; Vrettou, M.; Raabe, G. Angew. Chem., Int. Ed. 2005, 44, 4079
24. Cardova, A.; Watanabe, S. I.; Tanaka, F.; Notz, W.; Barbas, C. F., III J. Am. Chem. Soc. 2002, 124, 1866
25. The PMP-protected iminoesters have been used in organocatalyzed Mannich reactions. The protecting group PMP poses potential problems while deprotecting. The Boc-protected iminoesters were not suitable in our case. Hence, N -Boc-furylimine was employed in our study, which is easy to prepare and also hydrophilic in nature.
26. The dr values of 6, ent-6, 11, and ent-11 have been determined after chromatography of the corresponding reaction mixture (see the Supporting Information).
27. The crystallographic coordinates have been deposited with the Cambridge Crystallographic Data Centre; deposition no. 764863. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Rd., Cambridge CB2 1EZ, UK or via www.ccdc.cam.ac.uk/conts/retrieving.html.