Enantioselective rhodium enolate protonations. A new methodology for the synthesis of β2-amino acids

Organic Letters

Volumn 7, Issue 13, 2005, Pages 2571-2573

  Sibi, Mukund P ^a   Tatamidani, Hiroto ^a   Patil, Kalyani ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMINO ACID; BORONIC ACID DERIVATIVE; RHODIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACRYLATES; AMINO ACIDS; BORONIC ACIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 24944439352     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050630b     Document Type: Article

References (44)

1. (a) Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
2. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579.
3. Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada, K. J. Am. Chem. Soc. 2001, 123, 10774.
4. (a) Oi, S.; Moro, M.; Ono, S.; Inoue, Y. Chem. Lett. 1998, 83.
5. (b) Oi, S.; Moro, M.; Ito, H.; Honma, Y.; Miyano, S.; Inoue, Y. Tetrahedron 2002, 58, 91.
6. For recent reviews, see: (a) Hayashi, T. Synlett 2001, 879.
7. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
8. (c) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
9. For an example of addition to 1-nitrocyclohexene, see: Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
10. (a) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719.
11. (b) Reetz, M. T.; Moulin, D.; Gosberg, A. Org. Lett. 2001, 3, 4083.
12. (c) Chapman, C. J.; Wadsworth, K. J.; Frost, C. G. J. Organomet. Chem. 2003, 680, 206.
13. (d) Moss, R. J.; Wadsworth, K. J.; Chapman, C. J.; Frost, C. G. Chem. Commun. 2004, 1984.
14. (e) For Co-mediated reduction/protonation: Ohtsuka, Y.; Ikeno, T.; Yamada, T. Tetrahedron: Asymmetry 2003, 14, 967.
15. Racemic reactions: (f) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345, 353.
16. (g) Huang, T.-S.; Li, C.-J. Org. Lett. 2001, 3, 2037.
17. For a recent review, see: Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
18. Also see: Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983.
19. (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem., Int. Ed. 2002, 41, 2197.
20. (b) Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189.
21. (c) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700.
22. (d) Muñoz-Muñiz, O.; Juaristi, E. Tetrahedron 2003, 59, 4223.
23. (e) Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575.
24. (f) Seebach, D.; Schaeffer, L.; Gessier, F.; Bindschädler, P.; Jäger, C.; Josien, D.; Kopp, S.; Lelais, G.; Mahajan, Y. R.; Micuch, P.; Sebesta, R.; Schweizer, B. W. Helv. Chim. Acta 2003, 86, 1852.
25. Cryptophycins: (a) Subbaraju, G. V.; Golakoti, T.; Patterson, G. M. L.; Moore, R. E. J. Nat. Prod. 1997, 60, 302.
26. Biologically active β-peptides: (b) Werder, M.; Hauser, H.; Abele, S.; Seebach, D. Helv. Chim. Acta 1999, 82, 1774.
27. Sibi, M. P.; Patil, K. Angew. Chem., Int. Ed. 2004, 43, 1235.
28. For recent reviews on enantioselective H-atom transfer, see: (a) Sibi, M. P.; Manyem, S.; Zimmerman, J. Chem. Rev. 2003, 103, 3263.
29. (b) Sibi, M. P.; Porter, N. A. Acc. Chem. Res. 1999, 32, 163.
30. For examples of chiral Lewis acid-mediated H-atom transfer, see: (c) Sibi, M. P.; Asano, Y.; Sausker, J. B. Angew. Chem., Int. Ed. 2001, 40, 1293.
31. (d) Sibi, M. P.; Sausker, J. B. J. Am. Chem. Soc. 2002, 124, 984.
32. For recent reviews on enantioselective protonations, see: (a) Eames, J.; Weerasooriya, N. Tetrahedron: Asymmetry 2001, 12, 1.
33. (b) Duhamel, L.; Duhamel, P.; Plaquevent, J.-C. Tetrahedron: Asymmetry 2004, 15, 3653.
34. Also see: (c) Muñoz-Muñiz, O.; Juaristi, E. Tetrahedron Lett. 2003, 44, 2023.
35. Wadsworth, K. J.; Wood, F. K.; Chapman, C. J.; Frost, C. G. Synlett 2004, 2022.
36. For Heck reactions with α-methylamino acrylates, see: Huck, J.; Receveur, J.-M.; Roumestant, M.-L.; Martinez, J. Synlett 2001, 1467.
37. Takaya, Y.; Ogasawara, M.; Hayashi, T. Chirality 2000, 12, 469.
38. 2 complex at 100 °C gave the product in 66% yield and 42% ee. We have also observed that prolonged heating of the tert-butyl ester at 100°C leads to decomposition of the starting material.
39. JOSIPHOS = 1-[2-(diphenylphosphino)ferrocenyl]ethyl dicyclohexyl phosphine; MethylBOPhoz = (R)-N-methyl-N-diphenylphosphino-1-[S-2- (diphenylphosphino)ferrocenyl]ethylamine; SYNPHOS = [(5,6),-(5′,6′)- bis(ethylenedioxy)biphenyl-2,2′-diyl]bis(diphenylphosphine); DIFLUORPHOS = [(4,4′-bi-2,2-difluoro-1,3-benzodioxole)-5,5′diyl] bis(diphenylphosphine).
40. Product does not racemize under the reaction conditions.
41. Increasing the amount of phthalimide did not lead to enhancement of the chemical yield or selectivity.
42. Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. PNAS 2004, 101, 5799.
43. Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320.
44. Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187.