Rhodium-catalysed 1,4-additions in water: Synthesis of succinic esters and β2-amino acid derivatives

Synlett

Volumn , Issue 11, 2004, Pages 2022-2024

  Wadsworth, Kelly J ^a   Wood, Frances K ^a   Chapman, Christopher J ^a   Frost, Christopher G ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

2 amino acids; Boronic acids; Conjugate addition; Rhodium; Succinic esters

Indexed keywords

ALKENE DERIVATIVE; AMINO ACID DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; RHODIUM; WATER;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; SUBSTITUTION REACTION;

EID: 4544232366     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830880     Document Type: Article

References (29)

1. For detailed reviews, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
2. For detailed reviews, see: (a) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
3. (a) Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 722.
4. (b) Lautens, M.; Roy, A.; Fukouka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5538.
5. (a) Chapman, C. J.; Frost, C. G. Adv. Synth. Catal. 2003, 345, 353.
6. (b) For related work with organotin and bismuth reagents see: Huang, T.-S.; Li, C.-J. Org. Lett. 2001, 3, 2037.
7. (c) For recent work with potassium trifluoro(organo)borates see: Navarre, L.; Darse, S.; Genet, J.-P. Eur. J. Org. Chem. 2004, 69.
8. (a) Fournie-Zaluski, M. C.; Coulaud, A.; Bouboutou, R.; Chaillet, P.; Devin, J.; Waksman, G.; Costentin, J.; Roques, B. P. J. Med. Chem. 1985, 28, 1158.
9. (b) Moore, W. M.; Spilburg, C. A. Biochemistry 1986, 25, 5189.
10. (c) Buhlmayer, P.; Caselli, A.; Fuhrer, W.; Goschke, R.; Rasetti, V.; Rueger, H.; Stanton, J. L.; Criscione, L.; Wood, J. M. J. Med. Chem. 1988, 31, 1839.
11. (d) Iizuka, K.; Mamijo, T.; Kubota, T.; Akahane, K.; Umeyama, H.; Koso, Y. J. Med. Chem. 1988, 31, 704.
12. (e) Harada, H.; Yamaguchi, T.; Iyobe, A.; Tsubaki, A.; Kamijo, T.; Iizuka, K.; Ogura, K.; Kiso, Y. J. Org. Chem. 1990, 55, 1679.
13. (f) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1990, 31, 261.
14. (g) Heitsch, H.; Henning, R.; Kleemann, H.-W.; Linz, W.; Nickel, W.-U.; Ruppert, D.; Urbach, H.; Wagner, A. J. Med. Chem. 1993, 36, 2788.
15. (h) Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983.
16. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem. Int. Ed. 1998, 37, 1931.
17. 3): δ = 2.32 (3 H, m), 2.64 (1 H, dd, J = 8.7, 16.5 Hz), 2.91 (1 H, m), 3.58 (3 H, s), 3.63 (3 H, s), 6.00 (1 H, m), 6.30 (1 H, d, J = 15.6 Hz), 7.19 (4 H, s).
18. 2-amino acid synthesis see: (a) Duursma, A.; Minaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700. (b) Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575. (c) 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. (d) Sibi, M. P.; Patil, K. Angew. Chem. Int. Ed. 2004, 43, 1235.
19. 2-amino acid synthesis see: (a) Duursma, A.; Minaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700. (b) Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575. (c) 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. (d) Sibi, M. P.; Patil, K. Angew. Chem. Int. Ed. 2004, 43, 1235.
20. 2-amino acid synthesis see: (a) Duursma, A.; Minaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700. (b) Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575. (c) 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. (d) Sibi, M. P.; Patil, K. Angew. Chem. Int. Ed. 2004, 43, 1235.
21. 2-amino acid synthesis see: (a) Duursma, A.; Minaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700. (b) Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575. (c) 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. (d) Sibi, M. P.; Patil, K. Angew. Chem. Int. Ed. 2004, 43, 1235.
22. Basavaiah, D.; Krishnamacharyulu, M.; Rao, J. Synth. Commun. 2000, 30, 2061.
23. 3): δ = 2.80 (1 H, dd, J = 6.5, 14.0 Hz), 3.00 (1 H, dd, J =9.0, 14.1 Hz), 3.30 (1 H, m), 3.90 (1 H, dd, J = 6.3, 13.8 Hz), 4.05 (l H, dd, J = 8.1, 13.8 Hz), 5.00 (2 H, s), 7.05 (2 H, d, J = 8.4 Hz), 7.15 (2 H, m), 7.23 (3 H, m), 7.29 (2 H, d, J = 8.4 Hz), 7.70 (2 H, m), 7.80 (2 H, m).
24. Calmes, M.; Daunis, J.; Mai, N. Tetrahedron: Asymmetry 1997, 1641.
25. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.
26. For examples of enantioselective additions to α,β-dehydroamino acid derivatives, see: (a) Reetz, M. T.; Moulin, D.; Gosburg, A. Org. Lett. 2001, 3, 4083. (b) Chapman, C. J.; Wadsworth, K. J.; Frost, C. G. J. Organomet. Chem. 2003, 680, 206. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem. Int. Ed. 2004, 43, 719.
27. For examples of enantioselective additions to α,β-dehydroamino acid derivatives, see: (a) Reetz, M. T.; Moulin, D.; Gosburg, A. Org. Lett. 2001, 3, 4083. (b) Chapman, C. J.; Wadsworth, K. J.; Frost, C. G. J. Organomet. Chem. 2003, 680, 206. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem. Int. Ed. 2004, 43, 719.
28. For examples of enantioselective additions to α,β-dehydroamino acid derivatives, see: (a) Reetz, M. T.; Moulin, D.; Gosburg, A. Org. Lett. 2001, 3, 4083. (b) Chapman, C. J.; Wadsworth, K. J.; Frost, C. G. J. Organomet. Chem. 2003, 680, 206. (c) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem. Int. Ed. 2004, 43, 719.
29. Dixon, J. A.; Neiswender, D. D. Jr. J. Org. Chem. 1960, 25, 499.