Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1801-1804

  Katagiri, Nobuya ^a   Okada, Makoto ^a   Kaneko, Chikara ^a   Furuya, Toshio ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLGLYCINE; AMINO ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029869688     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00122-0     Document Type: Article

References (18)

1. Katagiri, N.; Kurimoto, A.; Yamada, A.; Sato, H.; Katsuhara, T.; Takagi, K.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1994, 281.
2. Two reaction pathways could be considered for the formation of nitrones (C), a [4+2] cycloaddition followed by a 1,2-migration, or a direct [3+2] cycloaddition. Quite recently, Birney and his co-worker proposed on the basis of the ab initio study that the reaction should proceed via the direct [3+2] cycloaddition. Ham S.; Birney D. M. Tetrahedron Lett. 1994, 44, 8113.
3. Katagiri, N.; Sato, H.; Kurimoto, A.; Okada, M.; Yamada, A.; Kaneko, C. J. Org. Chem. 1994, 59, 8101.
4. For recent papers dealing with the synthesis of optically active allylglycines, see: (a) Oppolzer, W.; Moretti, R.; Zhou, C. Helv. Chim. Acta. 1994, 77, 2363;
5. (b) Rose, J. E.; Leeson, P. D.; Gani, D. J. Chem. Soc. Perkin Trans, 1. 1995, 157. In these references, the amino acids were synthesized by the allylation of chiral glycine derivatives in the presence of butyl lithium followed by appropriate manipulation.
6. For a recent review dealing with the stereoselective synthesis of α-amino acids, see: Duthaler, R. O. Tetrahedron, 1994, 50, 1539.
7. 3).
8. 3).
9. In this reaction, the other isomer was also obtained in 14% yield, which would be formed by the reaction of nitrosoketene with isomenthone being contained as an impurity.
10. Full details of the X-ray data are to be deposited at the Cambridge Crystallographic Data Centre.
11. 3) δ: 2.16 (1H, ddd, J= 12.5, 11.5, 8.8 Hz, 4-Hb), 2.67 (1H, dd, J= 12.5, 3.8 Hz, 4-Ha), 3.84-3.92 (1H, m, 5-H), 4.14 (1H, d, J= 8.8 Hz, 3a-H).
12. 3OD) δ: 0.84 (1H, dd, J= 14.0, 8.7 Hz, CHH′TMS), 1.04 (1H, dd, J= 14.0, 5.5 Hz, CHH′TMS), 2.03 (1H, dt, J= 12.0, 10.0 Hz, 4-H), 2.35 (1H, ddd, J= 12.0, 6.0, 4.5 Hz, 4-H′), 3.79 (1H, dd, J= 10.0, 4.5 Hz, 3-H), 3.89-4.02(1H, m, 5-H).
13. 3OD) δ: 0.88 (1H, dd, J= 14.5, 7.0 Hz, CHH′TMS), 0.97 (1H, dd, J= 14.5, 7.0 Hz, CHH′TMS), 1.91 (1H, ddd, J= 15.0, 9.3, 4.2 Hz, 3-H), 2.03 (1H, ddd, J= 15.0, 6.7, 3.0 Hz, 3-H′), 3.75 (1H, dd, J= 6.7, 4.2 Hz, 2-H), 3.97-4.09 (1H, m, 4-H).
14. 2O)].
15. Black, S.; Wright, N. G. J. Biol. Chem. 1955, 213, 39.
16. 2O.
17. 3) δ: 2.13 (1H, ddd, J= 12.2, 11.1, 8.7 Hz, 4-Hb), 2.63 (1H, dd, J= 12.2, 4.0 Hz, 4-Ha), 3.73-3.86 (1H, m, 5-H), 4.17 (1H, d, J= 8.7 Hz, 3a-H).
18. Cramer, U.; Rehfeldt, A. G.; Spener, F. Biochemistry, 1980, 19, 3074.