Nucleophilic addition to an achiral dehydroalanine Schiff Base Ni(II) complex as a route to amino acids. A case of stereodetermining asymmetric protonation in the presence of TADDOL

Arkivoc

Volumn 2004, Issue 3, 2004, Pages 132-150

  Belokon, Yuri N ^a   Harutyunyan, Syuzanna ^a   Vorontsov, Evgeni V ^a   Peregudov, Alexander S ^a   Chrustalev, Viktor N ^a   Kochetkov, Konstantin A ^a   Pripadchev, Dmitriy ^a   Sagyan, Ashot S ^b   Beck, Albert K ^c   Seebach, Dieter ^c  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^b YEREVAN STATE UNIVERSITY   (Armenia)

^c ETH ZURICH   (Switzerland)

Author keywords

Amino acid; Asymmetric protonation; Michael addition; TADDOL

Indexed keywords

ALPHA,ALPHA,ALPHA',ALPHA' TETRAARYL 1,3 DIOXALAN 4,5 DIMETHANOL; AMINO ACID DERIVATIVE; DEHYDROALANINE; METHANOL DERIVATIVE; NICKEL COMPLEX; SCHIFF BASE; UNCLASSIFIED DRUG;

ADDITION REACTION; AMINO ACID SYNTHESIS; ARTICLE; ASYMMETRIC CATALYSIS; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PROTON TRANSPORT; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 2942587170     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. (a) Krause N.; Hoffmann-Röder A. Synthesis, 2001, 2, 171-196;
2. (b) Joshi, N. N.; Jha, S. C.; ARKIVOC, 2002, 7, 167-196;
3. (c) McDaid, P.; Chen, Y.; Deng, L. Angew. Chem. Int Ed. Engl. 2002, 41, 338;
4. (d) M. Jamaguchi, T. Shiraishi, and M. Hirama, J. Org. Chem., 1996, 4 61, 3520;
5. (e) Halland, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 2002, 67, 8331
6. (a) Corey , E. L.; Noe, M. C.; Xu, F. Tetrahedron Lett., 1998, 39, 5347;
7. (b) Shibuguchi, T.; Fukuta, Y.; Sekine, A.; Ohschima, T.; Shibasaki, M. Tetrahedron Lett., 2002, 43, 9539
8. Lygo, B.; Crosby, J.; Lowdon, T. R.;Peterson, J. A.; Wainwright, P. G. Tetrahedron, 2001, 57, 2403-2409
9. (a) Pracejus H.; Wilke F.-W.; Hanemann K. J. Prakt. Chem. 1977, 319, 219;
10. (b) Kumar A.; Salunkhe R. V.; Rane R. A.; Dike S. Y. J. Chem. Soc., Chem. Commun. 1991, 485;
11. (c) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043.
12. (a) Fehr C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2566-2587;
13. (b) Yanagisawa A.; Yamamoto H. in Comprhensive Asymmetric Catalysis (Eds. E. N. Jacobsen, A. Pflatz, H. Yamamoto), Springer Heidelberg, 1999, pp 1295-1306;
14. (c) Fehr C.; Stempf I.; Galindo J. Angew. Chem. Int. Ed. Engl. 1993, 32, 1042-1044;
15. (d) Yanagisawa A; Watanabe T.; Kikuchi T.; Yamamoto H. J. Org. Chem. 2000, 65, 2979-2983;
16. (e) Munoz-Muniz O.; Juaristi E. Tetrahedron Lett. 2003, 44, 2023-2026;
17. (f) Nishimura K.; Ono M.; Nagaoka Y.; Tomioka K. Angew. Chem. Int. Ed. Engl. 2001,40, 440-442.
18. Cox P. J.; Simpkins N. S. Tetrahedron: Asymmetry 1991, 2, 1.
19. Cuenca A.; Medio-Simon M.; Aguilar G.; Weibel D.; Beck A. K.; Seebach D. Helv. Chim. Acta 2000, 83, 3153-3161.
20. Belokon Y.; Kochetkov K.; Churkina T.; Ikonnikov N.; Chesnokov A.; Larionov O.; Singh I.; Virinder; Parmar S.; Vyskocil S.; Kagan H. J. Org. Chem. 2000, 65, 7041-7048.
21. Belokon Y. N.; Kochetkov K. A.; Churkina T. D.; Ikonnikov N. S.; Larionov O. V.; Harutyunyan S. R.; Nort M.; Viscochil S.; Kagan H. Angew. Chem. Int. Ed. 2001, 40, 1948
22. (a) Jim A.; Vidal Y.; Viallefont; Martinez J. Tetrahedron: Asymmetry 2002, 13, 503-510;
23. (b) Balsamini C.; Diamantini G.; Duranti A.; Spadoni G.; Tontini A. Synthesis 1994, 370-372;
24. (c) Tarzia G.; Balsamini C.; Diamantini G.; Duranti A. Synthesis 1988, 370-372;
25. (d) Gativela C.; Lopes P.; Majoral J. A. Tetrahedron: Asymmetry 1991, 12, 1295-1304.
26. (e) Belokon' Y. N.; Sagyan A. S.; Djamgaryan S.; Bakhmutov V. I.; Belikov V. Tetrahedron 1988, 17, 5507-5514
27. (f) Gasanov R. G.; Il'inskaya L. V.; Misharin M. A.; Maleev V. I.; Raevski N. I.; Ikonnikov N. S.; Kuzmina S. A.; Belokon' Y. N. J. Chem. Soc. Perkin. Trans. 1 1994, 3343-3348;
28. Terekhova, M. I.; Belokon, Y. N.; Maleev, V. I;. Chernoglazova, N. I.; Kochetkov, K. A.; Belikov, V. M.; Petrov, E. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 905 [Bull Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 824 (Engl. Transl.)].
29. Terekhova, M. I.; Belokon, Y. N.; Maleev, V. I;. Chernoglazova, N. I.; Kochetkov, K. A.; Belikov, V. M.; Petrov, E. S. Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 905 [Bull Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 824 (Engl. Transl.)].
30. Seebach, D., Beck, A. K.; Heckel, A. Angew. Chem. Int. Ed. 2001, 40, 92-138
31. SMART and SAINT, Release 5.0. Area detector control and integration software. Bruker AXS,Analytical X-Ray Instruments, Madison, Wisconsin, USA, 1998.
32. Sheldrick, G. M. SHELXTL. V5.10. Bruker AXS Inc. Madison. WI-53719. USA. 1997.
33. Jpn. Kokai Tokkyo Koho (1998), 4 pp.CODEN: JKXXAF JP 10001468 A21998.