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Extra info for Asymmetric Synthesis and Application of α-Amino Acids
The reagents employed were the aspartate semialdehyde 28, the glycosylated ketoester 29, and the already exploited valuable aminocrotonate 25. This reaction was carried out under M W irradiation and processed using the same orchestrated sequence of polymer supported reagents illustrated in Scheme 7. The target amino ester 30 was isolated in 68% yield. The efficiency of the routes illustrated in Schemes 7 and 8 was validated by preparation of other amino acids so that a collection of eight compounds shown in Figure 3 was obtained in which the elements of diversity were: (i) the galacto and gluco configurations of the pyranose ring, (ii) the a- and P-configurations at the anomeric center, and (iii) the positions of the carbohydrate and amino acid residues in the pyridine ring.
Marshall, G . R. J. Am. Chem. Soc. 1988, 110, 5875-5880. ; Aldhoun, M . , unpublished results. ; Vilarrasa, J. Angew. Chem. Int. Ed. 2007, 46, 3926-3930. Demko, Z. ; Sharpless, K . B . Angew. , Int. Ed. Engl. 2002, 41, 2110-2113. ; Marra, A . Tetrahedron 2007, 63, 6339-6345. Dondoni, A . ; Massi, A . Acc. Chem. Res. 2006, 39, 451-463 and references therein. ; Aldhoun, M . J. Org. Chem. 2007, 72, 7677-7687. C 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30. C Chapter 3 Asymmetric Synthesis of Amino Acids with a Tetrasubstituted Carbon Center via Memory of Chirality Takeo Kawabata Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan Asymmetric synthesis of amino acid derivatives with a tetrasubstituted carbon center via memory of chirality is described.
Conclusion Asymmetric intermelucular and intramolecular alkylation of a-amino acid derivatives via memory of chirality has been described. Chiral enaoltes with dynamic axial chirality are responsible for the asymmetric induction.