Diastereoselective additions of organolithium and organomagnesium reagents to the C=N bond of a chiral, cyclic nitrone derived from erythrulose

Tetrahedron Letters

Volumn 39, Issue 20, 1998, Pages 3237-3240

  Marco, J Alberto ^a   Carda, Miguel ^b   Murga, Juan ^b   Portolés, Raul ^b   Falomir, Eva ^b   Lex, Johann ^c  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITAT JAUME I   (Spain)

^c UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM; ORGANOLITHIUM COMPOUND;

AMINO ACID SEQUENCE; ARTICLE; CATALYST; CHIRALITY; CHROMATOGRAPHY; CRYSTALLIZATION; STEREOCHEMISTRY;

EID: 0032516306     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00400-6     Document Type: Article

References (24)

1. 1. (a) Harada, K. in The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; John Wiley and Sons: New York; 1970; Chapt. 6, pp 255-298.
2. (b) Tennant, G. in Comprehensive Organic Chemistry; Barton, D.H.R., Ollis, W.D., Eds.; Pergamon Press: Oxford, 1979; Vol. 2, pp 385-590.
3. (c) Yamaguchi, M. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 325-353.
4. (d) Volkmann, R.A. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, pp 355-396.
5. (e) Kleinman, E.F. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 893-951.
6. (f) Kleinman, E.F. and Volkmann, R.A. in Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, pp 975-1006.
7. (g) Risch, N.; Arend, M. in Houben-Weyl's Methods of Organic Chemistry. Stereoselective Synthesis; Helmchen, G., Hoffmann, R.W., Mulzer, J., Schaumann E., Eds.; Georg Thieme Verlag: Stuttgart, 1996; Vol. 3, pp. 1833-1929.
8. 2. a) Jäger, V.; Hümmer, W.; Stahl, U.; Gracza, T. Synthesis 1991, 769-776, and references cited therein.
9. (b) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360-366.
10. 3. (a) Williams, R.M. Synthesis of Optically Active α-Aminoacids; Pergamon Press: Oxford, 1989.
11. (b) Williams, R.M.; Hendrix, J.A. Chem. Rev. 1992, 92, 889-917.
12. (c) Duthaler, R.O. Tetrahedron 1994, 50, 1539-1650.
13. 4. Gante, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1699-1720.
14. 5. Murga, J., Ph.D. Thesis, Universitat Jaume I, 1996. Part of the work described in this Ph.D. Thesis has been recently published as a preliminary communication: Marco, J.A.; Carda, M.; Murga, J.; González, F.; Falomir, E. Tetrahedron Lett. 1997, 38, 1841-1844. A full acount of this work has recently been sent to publication.
15. 6. For a recent, short review on the topic of α,α-disubstituted α-aminoacids, see: Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
16. 7. Dequeker, E.; Compernolle, F.; Toppet, S.; Hoornaert, G. Tetrahedron 1995, 51, 5877-5890.
17. 8. Crystallographic data of compounds 4 and 5 have been deposited in the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K., and may be requested from the Director of this Centre.
18. 9. See, for example: (a) Chang, Z.-Y.; Coates, R.M. J. Org. Chem. 1990, 55, 3464-3474.
19. (b) Basha, A., Henry, R.; McLaughlin, M.A.; Ratajczyk, J.D.; Wittenberger, S.J. J. Org. Chem. 1994, 59, 6103-6106.
20. (c) Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F.L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505-520.
21. (d) Merino, P.; Lanaspa, A.; Merchán, F.L., Tejero, T. J. Org. Chem. 1996, 61, 9028-9032.
22. (e) Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
23. 10. (a) Torssell, K.B.G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH, 1988.
24. (b) Confalone, P.N.; Huie, E.M., Org. React. 1988, 36, 1-173.