Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5831-5835

  O'Donnell, Martin J ^a   Delgado, Francisca ^a   Drew, Mark D ^a,c   Pottorf, Richard S ^a,d   Zhou, Changyou ^a,e   Scott, William L ^b  

^a INDIANA UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c SANOFI   (France)

^d Provid Research   (United States)

^e MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Amino acid derivatives; Amino acids; Boron; Boron compounds; Solid phase synthesis

Indexed keywords

AMINO ACID DERIVATIVE; CATION; GLYCINE; RESIN;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLID STATE;

EID: 0033529833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01101-6     Document Type: Article

References (23)

1. O'Donnell, M. J.; Esikova, I. A.; Mi, A.; Shullenberger, D. F.; Wu, S. In Phase-Transfer Catalysis: Mechanisms and Synthesis; (ACS Symposium Series 659); Halpern, M. E., Ed., Amino Acid and Peptide Synthesis Using Phase-Transfercatalysis; ACS: Washington DC, 1997; Chapter 10.
2. O'Donnell, M. J.; Esikova, I. A.; Mi, A.; Shullenberger, D. F.; Wu, S. In Phase-Transfer Catalysis: Mechanisms Andsynthesis; (ACS Symposium Series 659); Halpern, M. E., Ed., Amino Acid and Peptide Synthesis Using Phase-Transfer Catalysis; ACS: Washington DC, 1997; Chapter 10.
3. O'Donnell, M. J.; Bennett, W. D. Tetrahedron 1988, 44, 5389-5401 and references cited therein.
4. (a)O'Donnell, M. J.; Falmagne, J.-B. Chem. Commun. 1985, 1168-1169.
5. (b)O'Donnell, M. J.; Lawley, L. K.; Pushpavanam, P. B.; Burger, A.; Bordwell, F. G.; Zhang, X.-M. Tetrahedron Lett. 1994, 35, 6421-6424.
6. Catalytic enantioselective syntheses with amino acid anionic equivalents: (a)O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355.
7. (b)O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775-8778 and references cited therein.
8. Catalytic enantioselective syntheses with a glycine cationic equivalent: O'Donnell, M. J.; Chen, N.; Zhou, C.; Murray, A.; Kubiak, C. P.; Yang, F.; Stanley, G. G. J. Org. Chem. 1997, 62, 3962-3975.
9. For a recent short review on the preparation of amino acids by asymmetric PTC reactions, see: O'Donnell, M. J. Phases; SACHEM: Austin, TX, 1998; Issue 4, pp. 5-8.
10. (a)Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598.
11. (b)Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
12. (c)Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350.
13. (a)O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070-6071.
14. (b)O'Donnell, M. J.; Delgado, F.; Pottorf, R. S. Tetrahedron 1999, 55, 6347-6362 and references cited therein.
15. Brown, H. C.; Rogic, M. M.; Rathke, M. W.; Kabalka, G. W. J. Am. Chem. Soc. 1968, 90, 818-820.
16. (a)Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: London, 1988; pp. 14-15, 63-65, 261-273.
17. (b)Li, N.-S.; Yu, S.; Kabalka, G. W. Organometallics 1997, 16, 709-712 and references cited therein.
18. For a large-scale preparation of see Ref.4 in O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166.
19. (a)Knights, E. V.; Brown, H. C. J. Am. Chem. Soc. 1968, 90, 5281-5283.
20. (b)Scouten, C. G.; Brown, H. C. J. Org. Chem. 1973, 38, 4092-4094.
21. Scott, W. L.; Schonegg, R. A.; Cwi, C. L. US Patent, 1998, 5 785 927.
22. 3CN): 7a: 1.02 (t, 3H, J=7.4 Hz); 1.84-2.11 (m, 2H); 4.61 (td, 1H, J=7.4 and 5.2 Hz); 7.70 (app. t, 1H, J=7.4 Hz); 7.85 (app. t, 1H, J=7.4 Hz); 8.02 (d, 1H, J=8.1 Hz); 8.16 (d, 1H, J=8.8 Hz); 8.20 (d, 1H, J=8.8 Hz); 8.47 (d, 1H, J=8.8 Hz); 8.65 (d, 1H, J=5.2 Hz). 7g: 0.90-2.05 (m, 13H); 4.72 (app. q, 1H, J=7.7 Hz); 7.71 (app. t, 1H, J=7.4 Hz); 7.87 (td, 1H, J=8.1 and 1.5 Hz); 8.02 (d, 1H, J=8.1 Hz); 8.19 (app. t, 2H, J=8.1 Hz); 8.48 (d, 1H, J=8.1 Hz); 8.60 (d, 1H, J=8.1 Hz). 7i: 1.10-1.34 (m, 4H); 1.64-1.79 (m, 6H); 1.90-2.05 (m, 1H); 4.58 (dd, 1H, J=8.5 and 5.5 Hz); 7.72 (app. t, 1H, J=7.4 Hz); 7.87 (app. t, 1H, J=7.4 Hz); 8.03 (d, 1H, J=8.1 Hz); 8.20 (app. t, 2H, J=8.1 Hz); 8.51 (d, 1H, J=8.1 Hz); 8.63 (d, 1H, J=8.1 Hz). 71: 1.11 (s, 9H); 4.50 (d, 1H, J=8.8 Hz); 7.70 (app. t, 1H, J=7.4 Hz); 7.85 (dd, 1H, J=7.4 and 8.5 Hz); 8.02 (d, 1H, J=8.1 Hz); 8.19 (app. t, 2H, J=8.5 Hz); 8.48 (d, 1H, J=8.8 Hz); 8.70 (d, 1H, J=8.1 Hz). 7m: 0.45-0.72 (m, 4H); 1.26-1.42 (m, 1H); 3.99 (app. t, 1H, J=8.5 Hz); 7.71 (td, 1H, J=8.1 and 1.5 Hz); 7.86 (td, 1H, J=7.7 and 1.5 Hz); 8.02 (d, 1H, J=8.1 Hz); 8.18 (d, 1H, J=8.1 Hz); 8.19 (d, 1H, J=8.1 Hz); 8.47 (d, 1H, J=8.1 Hz); 8.71 (d, 1H, J=5.1 Hz).
23. 3CN): 7a (R′CO=Fmoc): 0.94 (t, 3H, J=7.4 Hz); 1.68 (sext, 1H, J=7.4 Hz); 1.81 (sext, 1H, J=7.4 Hz); 4.06 (td, 1H, J=7.4 and 5.2 Hz); 4.25 (dd, 1H, J=13.6 and 7.4 Hz); 4.33 (d, 2H, J=7.4 Hz); 5.98 (d, 1H, J=5.2 Hz); 7.33-7.45 (m, 4H); 7.59-7.71 (m, 2H); 7.84 (d, 2H, J=7.4 Hz). 7a (R′CO=Cbz): 0.93 (t, 3H, J=7.4 Hz); 1.68 (sext, 1H, J=7.4 Hz); 1.82 (sext, 1H, J=7.4 Hz); 4.07 (td, 1H, J=8.1 and 5.2 Hz); 5.07 (s, 2H); 5.92 (d, 1H, J=5.2 Hz); 7.24-7.40 (m, 5H).