A three-step, highly enantioselective synthesis of (R)-2-methyl tryptophane ethyl ester: Comparison with chemical resolution

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3861-3864

  Solladié Cavallo, Arlette ^a   Schwarz, Johanes ^a   Mouza, Cyrille ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLTRYPTOPHANE ETHYL ESTER; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DIASTEREOISOMER; ENANTIOMER; SYNTHESIS;

EID: 0032575184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00633-9     Document Type: Article

References (26)

1. 1 Andersen M. Science 1945, 101, 565
2. 2 a) Rydon H..N. J. Chem. Soc. 1948, 705 (R=Me).
3. b) Kissman H.M., Witkop B. J. Am. Chem, Soc, 1953, 75, 1967 (R=Ph).
4. c) Jaeger E., Thamm P., Knof S., Wunsch E., Hoppe-Seyler's Z. Physiol. Chem. 1978, 359 1629 (R= tBu).
5. 11, tBu, Pyridyl).
6. 3 Discovered by Wagner in 1894 (Ber. Chem. Gessels. 27, 2272) the hydroxypinanone 1 was then described by Delepine M. (Bull. Soc. Chim. Fr. 1937, 4, 1669), Kuwata (J. Am. Chem. Soc. 1937, 59, 2509) and our group (Bull. Soc. Chim. Fr. 1989, 544 and Tetrahedron Lett. 1997, 38, 5851). This compound was used for the first time as chiral auxiliary by Yamada S.I, Shioiri T. et al in 1976 (ref. 6a).
7. 3 Discovered by Wagner in 1894 (Ber. Chem. Gessels. 27, 2272) the hydroxypinanone 1 was then described by Delepine M. (Bull. Soc. Chim. Fr. 1937, 4, 1669), Kuwata (J. Am. Chem. Soc. 1937, 59, 2509) and our group (Bull. Soc. Chim. Fr. 1989, 544 and Tetrahedron Lett. 1997, 38, 5851). This compound was used for the first time as chiral auxiliary by Yamada S.I, Shioiri T. et al in 1976 (ref. 6a).
8. 3 Discovered by Wagner in 1894 (Ber. Chem. Gessels. 27, 2272) the hydroxypinanone 1 was then described by Delepine M. (Bull. Soc. Chim. Fr. 1937, 4, 1669), Kuwata (J. Am. Chem. Soc. 1937, 59, 2509) and our group (Bull. Soc. Chim. Fr. 1989, 544 and Tetrahedron Lett. 1997, 38, 5851). This compound was used for the first time as chiral auxiliary by Yamada S.I, Shioiri T. et al in 1976 (ref. 6a).
9. 3 Discovered by Wagner in 1894 (Ber. Chem. Gessels. 27, 2272) the hydroxypinanone 1 was then described by Delepine M. (Bull. Soc. Chim. Fr. 1937, 4, 1669), Kuwata (J. Am. Chem. Soc. 1937, 59, 2509) and our group (Bull. Soc. Chim. Fr. 1989, 544 and Tetrahedron Lett. 1997, 38, 5851). This compound was used for the first time as chiral auxiliary by Yamada S.I, Shioiri T. et al in 1976 (ref. 6a).
10. 3 Discovered by Wagner in 1894 (Ber. Chem. Gessels. 27, 2272) the hydroxypinanone 1 was then described by Delepine M. (Bull. Soc. Chim. Fr. 1937, 4, 1669), Kuwata (J. Am. Chem. Soc. 1937, 59, 2509) and our group (Bull. Soc. Chim. Fr. 1989, 544 and Tetrahedron Lett. 1997, 38, 5851). This compound was used for the first time as chiral auxiliary by Yamada S.I, Shioiri T. et al in 1976 (ref. 6a).
11. 3) δ : 11.8 ; 14.1; 30.1; 55.3; 60.9; 107.1; 110.2; 118.0; 119.4; 121.2; 128.3; 132.6; 135.3; 175.4. All the samples exhibited correct elemental analyses.
12. 5 Gilchrist T.L., Lingham D.A., Roberts T.G. J.C.S. Ckem-Comm. 1979, 1089.
13. 6 a) Yamada S.I., Oguri T., Shioiri T., JCS Chem. Comm. 1976, 136.
14. b) Solladié-Cavallo A., Schwarz J., Burger V. Tetrahedron : Asymm. 1994, 5, 1621.
15. 7 Merck Silicagel 60 (0.5-40 μm) ; solvent : hexane/ether 2/1 to 1/9 ; 15 mm Hg vacuum at the botton of the column.
16. 8 a) Oguri T., Kawai N., Shioiri T., Yamada S. Chem. Pharm. Bull 1978, 26, 803.
17. b) El Achqar A., Boumzebra M., Roumestant M.L., Viallefont P. Tetrahedron, 1988, 44, 5319 (cf p. 5321).
18. c) Solladié-Cavallo A., Simon-Wermeister M.C, Tetrahedron Lett. 1989, 30, 6011.
19. 9 Solladié-Cavallo A., Simon-Wermeister M.C., Schwarz J., Organometallics, 1993, 12, 3743.
20. 2 was added because with analogues of benzyl halides the diastereoselectivities at -78°C are already high, ≥ 90%.
21. 3) δ : 11.8; 14.1 ; 21.4 ; 27.0 ; 27.7 ; 27.9; 28.5 ; 32.6 ; 37.8 ; 38.1 ; 49.8 ; 60.9 ; 62.5 ; 76.3 ; 107.4 110.1 ; 117,7 ; 119.2 ; 120.9 ; 128.3 ; 132.4 ; 135.2 ; 172.1 ; 178.2.
22. 12 Dave V., Warnhof E.W. Can. J. Chem. 1971, 49, 194.
23. 13 a) Vice S.F., Copeland C., Forsey S.P., Dmitrienko G.I. Tetrahedron Lett. 1985, 26, 5253.
24. b) Vice S.F., Dmitrienko G.I. Can. J. Chem. 1982, 60, 1233.
25. 3 system disappeared and is replaced by a singlet at 3.04 for MeQ. All other δ are very similar.
26. 2X signal is at 4.77 (s. 2H).