Cycloadditions of aromatic imines to enantiomerically pure stabilized azomethine ylids: Construction of threo (2S,3R)-3-aryl-2,3-diamino acids

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 475-478

  Alker, David ^a   Harwood, Laurence M ^b   Williams, C Eleri ^c  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

^c UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 ARYL 2,3 DIAMINO ACID; DIAMINO ACID; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; SPECTROSCOPY;

EID: 0032576810     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10580-9     Document Type: Article

References (17)

1. 1. Alker, D.; Harwood, L. M.; Williams, C. E. Tetrahedron, 1997, 53, 12671 and references cited therein.
2. 2. Harwood, L. M.; Macro, J.; Watkin, D.; Williams, C. E.; Wong, L. F. Tetrahedron :Asymm., 1992, 1127.
3. 3. For example see: Ito, K.; Saito, K.; Takahashi, K. Heterocycles, 1993, 36, 21; Marrs, C. M. ; Trost, B. M. J. Am. Chem. Soc., 1993,115, 6636; Chastanet, J.; Roussi, G. J. Org. Chem, 1988, 53, 3808.
4. 3. For example see: Ito, K.; Saito, K.; Takahashi, K. Heterocycles, 1993, 36, 21; Marrs, C. M. ; Trost, B. M. J. Am. Chem. Soc., 1993,115, 6636; Chastanet, J.; Roussi, G. J. Org. Chem, 1988, 53, 3808.
5. 3. For example see: Ito, K.; Saito, K.; Takahashi, K. Heterocycles, 1993, 36, 21; Marrs, C. M. ; Trost, B. M. J. Am. Chem. Soc., 1993,115, 6636; Chastanet, J.; Roussi, G. J. Org. Chem, 1988, 53, 3808.
6. 4. Mohan, R.; Chou, Y. L.; Bihovsky, R.; Lumma, W. C. J. Med. Chem., 1991, 34, 2402.
7. 5. Herranz, R.; Vinuesa, S.; Castro-Pichel, J. Perez, C., Garcia-Lopez, M. T. J. Chem. Soc., Perkin Trans 1, 1992, 1825.
8. 6. For example see: (a) Ali, R. M.; Khan, N. H. Synth. Commun., 1978, 8, 497
9. (b) Rakshinda, M. A.; Khan, N.H. Synth Commun., 1979, 9, 351; 360
10. (c) Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. J. Am. Chem. Soc., 1985, 107, 7105
11. (d) Dunn, P. J.; Häner, R., Rapoport, H. J. Org. Chem., 1990, 55, 5017
12. (e) Pfammatter, E.; Seebach, D. Ann. Chem., 1991, 1323
13. (f) Es-Sayed, M.; Gratowski, C.; Krass, N.; Meyers, A.; de Meijere, A. Synlett, 1992, 963
14. (g) Bellus, D.; Ernst, B.; Gonda, J.; Heiland, A-C. Synthesis, 1993, 1323
15. (h) Burke, A. J.; Davies, S. G.; Hedgecock, C. J. Synlett, 1996, 621.
16. 6 requires 551 1931, found 551.1972; [Ot]024 -43.5 (c 0.85, CHCl3). (4e) m.p. 53-55 0C; Found C, 75.07, H, 5.37, N, 5.41 %, C3IH26N2O2F2 requires C, 74*.83, H, 5.47, N, 5.63 %; vmax (KBr disc) I 751 cnr1; 0H (500 MHz, CDCl3) 7.60 (dd, / 8.6, / 5.5 Hz, 2H), 7.01-6.92 (m, 7H), 6.84-6.77 (m, 5H), 6.60-6.55 (m, 4H), 4.56 (d, / 6.3 Hz, IH), 3.87 (s, IH), 3.66 (d, / 6.3 Hz, IH) 3.51-3.48 (m, 2H), 3.47 (d, 13.7 Hz, IH), 3.32 (d, / 14.0 Hz, IH), 3.20 (dd, y 8.1, J 6.7 Hz, IH); n.O.e. H2 → H9 (11.0%), H7 → H9 (4.6%); ôc (125.7 Hz, CHCl3) 171.6, 130.1, 136.6, 135.3, 134.9, 131.3, 130.3, 130.1, 128.2, 128.1, 127.9, 127.7, 127.4, 115.8, 115.3, 114.9, 114.5, 86.7, 71.1, 65.8, 65.4, 61.7, 51.5; m/z (CI1 NH3) 497 (MH+),[a]D20 -49.0 (c 1.0, CHCl3).
17. 8. (Sb) OH (500 MHz, D2O) 7.48-7.25 (m, 5H), 4.64 (d, / 5.2 Hz, IH), 4.64 (d, / 5.2 Hz, IH); SC (125.7 MHz, D2O) 169.3, 151.7, 129.8, 128.8, 126.9, 53.0, 52.4; m/z (CI, NH3) 181 (MH+), C9H]3N2O2 requires 181.0977, found 181.0979; [a]D24 -0.9 (c 1.0, H2O). (Sc) m.p. 185-1860C (dec.); ÔH (500 MHz, D2O) 7.37 (d, / 8.8Hz, 2H), 7.05, (d, / 8.7 Hz, 2H), 4.66 (d, / 5.1 Hz, IH), 4.15 (d, / 5.1 Hz, IH), 3.82 (s, 3H); 5c (125.7 MHz, D2O) 170.1, 159.4, 128.5, 122.1, 114.2, 54.5, 53.5, 52.3; m/z (Electrospray) 211 (MH+), 150, C]0H]5N2O3 requires 211.1083, found 211.1071; [a]D25 -14.6 (c 1.0, H2O). (Sd) Pale yellow powder; vmax (KBr disc) 3431, 1679 1631 cm-1; OH (500 MHz, D2O) 7.25 (d, / 8.5 Hz, 2H), 6.88 (d, / 8.5 Hz, 2H), 4.66 (d, / 4.8 Hz, IH), 4.23 (d, / 4.9 Hz, IH); m/z (CI, NH3) C9H14N3O2 requires 196.1086, found 196.1089; [a]D24 -5.2 (c 0.25, H2O). (Se) m.p. 190-195 0C (dec.); OH (500 MHz, D2O) 7.47-7.42 (m, 2H), 7.23 (t, / 8.8Hz, 2H), 4.77 (d, / 4.9 Hz, IH), 4.23 (d, / 4.9 Hz, IH); 5C (125.7 MHz, D2O) 171.1, 131.1, 130.6, 128.3, 117.1, 54.7, 53.4; m/z (DCI, NH3) 199 (MH+), 124, C9H]2N2O2F requires 199.0883, found 199.0892; [a]D25 -7.8 (c 0.5, H2O).