Asymmetric synthesis of (S)-α-methyl α-amino acids by alkylation of chiral 3,6-dihydro-2h-1,4-oxazin-2-ones using unactivated alkyl halides and organic bases

Tetrahedron Asymmetry

Volumn 9, Issue 16, 1998, Pages 2769-2772

  Chinchilla, Rafael ^a   Galindo, Nuria ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 OXAZINE DERIVATIVE; ALPHA AMINO ACID; AMINO ACID DERIVATIVE; BASE; HALIDE; IODIDE; LITHIUM;

ALKYLATION; AMINO ACID SYNTHESIS; CHIRALITY; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; REVIEW;

EID: 0032555624     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00288-2     Document Type: Article

References (24)

1. Some examples: (a) Jung, M. J. In Chemistry and Biochemistry of the Amino Acids, Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; pp. 227-245. (b) Altmann, K. H.; Altmann, E.; Mutter, M. Helv. Chim. Acta 1992, 75, 1198-1210. (c) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
2. Some examples: (a) Jung, M. J. In Chemistry and Biochemistry of the Amino Acids, Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; pp. 227-245. (b) Altmann, K. H.; Altmann, E.; Mutter, M. Helv. Chim. Acta 1992, 75, 1198-1210. (c) Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
3. Some examples: (a) Jung, M. J. In Chemistry and Biochemistry of the Amino Acids, Barrett, G. C., Ed.; Chapman and Hall: New York, 1985; pp. 227-245. (b) Altmann, K. H.; Altmann, E.; Mutter, M. Helv. Chim. Acta 1992, 75, 1198-1210. Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
4. Recent reviews: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon Press: Oxford, 1989. (b) Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748. (e) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
5. Recent reviews: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon Press: Oxford, 1989. (b) Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748. (e) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
6. Recent reviews: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon Press: Oxford, 1989. (b) Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748. (e) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
7. Recent reviews: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon Press: Oxford, 1989. (b) Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748. (e) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
8. Recent reviews: (a) Williams, R. M. Synthesis of Optically Active Amino Acids, Pergamon Press: Oxford, 1989. (b) Heimgartner, H. Angew. Chem. Int. Ed. Engl. 1991, 30, 238-264. Duthaler, R. O. Tetrahedron 1994, 50, 1540-1650. (d) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 2708-2748. (e) Wirth, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 225-227.
9. Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Angew. Chem. Int. Ed. Engl. 1997, 36, 995-997.
10. Abellán, T.; Nájera, C.; Sansano, J. M. Tetrahedron: Asymmetry, in press.
11. t, NaH) under different reaction conditions failed.
12. Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmitt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435-2454, and references cited therein.
13. The use of BEMP as base has proved to be effective in the recent alkylation of the resin-bound benzophenone imine of glycine with unactivated alkyl halides: (a) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166. (b) O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070-6072.
14. The use of BEMP as base has proved to be effective in the recent alkylation of the resin-bound benzophenone imine of glycine with unactivated alkyl halides: (a) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C.; Scott, W. L.; Cwi, C. L. Tetrahedron Lett. 1997, 38, 7163-7166. (b) O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070-6072.
15. 2).
16. For a recent discussion on lithium salt effects in organic synthesis, see: Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods 1995, VCH Publishers: Basel, 1995; Vol. 7, pp. 1-178.
17. 4), evaporated in vacuo (15 torr) and the residue purified by flash chromatography on silica gel (Hex/EtOAc mixtures) affording compounds 3.
18. 2O): Kruizinga, W. H.; Bolster, J.; Kellog, R. M.; Kamphuis, J.; Boesten, W. H. J.; Meijer, E. M.; Schoemaker, H. E. J. Org. Chem. 1988, 53, 1826-1827.
19. 3) δ: 19.8, 21.1, 21.8, 22.9, 27.8, 35.5, 50.8, 61.2, 122.4, 128.1, 128.3, 129.2, 134.8, 139.3, 169.1.
20. For example, (S)-α-methyrproline has been shown to stabilize the type-I β-turn conformations in peptides containing the Asn-Pro-Asn-Ala (NPNA) motif of the Plasmodium falciparum circumsporozoite protein: Bisang, C.; Weber, C.; Inglis, J.; Schiffer, C. A.; van Gunsteren, W. F.; Jelesarov, I.; Bosshard, H. R.; Robinson, J. A. J. Am. Chem. Soc. 1995, 117, 7904-7915.
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24. 25 -72.1 (c 1, MeOH).