Stereodivergent Approach to β-Hydroxy α-Amino Acids from C2-Symmetrical Alk-2-yne-1,4-diols

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4511-4514

  Amador, Marta ^a   Ariza, Xavier ^a   Garcia, Jordi ^a   Sevilla, Sara ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYLEUCINE; 3-HYDROXYLEUCINE; AMINO ACID; DRUG DERIVATIVE; LEUCINE; SERINE;

ARTICLE; CATALYSIS; CHEMISTRY; CONFORMATION; CYCLIZATION; SYNTHESIS;

AMINO ACIDS; CATALYSIS; CYCLIZATION; LEUCINE; MOLECULAR CONFORMATION; SERINE;

EID: 0037069705     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0270428     Document Type: Article

References (37)

1. Barrett G. C. Chemistry and Biochemistry of Amino Acids; Chapman and Hall: London, 1985.
2. (a) Nagarajan, R. Glycopeptide Antibiotics; Marcel-Dekker: New York, 1994.
3. (b) See also ref 2 in: Blaskovich, M. A.; Evindar, G.; Rose, N. G. W.; Wilkinson, S.; Lou, Y.; Lajoie, G. A. J. Org. Chem. 1998, 63, 3631-3646.
4. Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids. Wiley: New York, 1987.
5. (a) Miller, M. J. Acc. Chem. Res. 1986, 19, 49-56.
6. (b) Labia, R.; Morin, C. J. Antibiot. 1984, 37, 1103-1129.
7. (c) Floyd, D. M.; Fritz, A. W.; Pluscee, J.; Weaver, E. R.; Cimarusti, C. M. J. Org. Chem. 1982, 47, 5160-5167.
8. (a) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
9. (b) Duthaler, R. O. Tetrahedron 1994, 50, 1539-1650.
10. (c) Chapter 8 in ref 1.
11. See, for example: (a) Shao, H.; Goodman, M. J. Org. Chem. 1996, 61, 2582-2583. (b) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640. Schmidt, U.; Respondek, M.; Lieberknecht, A.; Werner, J.; Fischer, P. Synthesis 1989, 256-261.
12. See, for example: (a) Shao, H.; Goodman, M. J. Org. Chem. 1996, 61, 2582-2583. (b) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640. Schmidt, U.; Respondek, M.; Lieberknecht, A.; Werner, J.; Fischer, P. Synthesis 1989, 256-261.
13. See, for example: (a) Shao, H.; Goodman, M. J. Org. Chem. 1996, 61, 2582-2583. (b) Jung, M. E.; Jung, Y. H. Tetrahedron Lett. 1989, 30, 6637-6640. (c) Schmidt, U.; Respondek, M.; Lieberknecht, A.; Werner, J.; Fischer, P. Synthesis 1989, 256-261.
14. (a) MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1883-1886.
15. (b) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843-3846.
16. (c) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
17. (a) Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H.; J. Am. Chem. Soc. 1989, 111, 9134-9135.
18. (b) Genet, J. P.; Pinel, C.; Mallart, S.; Juge, S.; Thorimbert, S.; Laffitte, J. A. Tetrahedron: Asymmetry 1991, 2, 555-567.
19. Kimura, T., Vassilev, V. P.; Shen, G.-J.; Wong, C.-H. J. Am. Chem. Soc. 1997, 119, 11734-11742.
20. Some remarkable exceptions are: (a) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888. (b) Kuwano, R.; Okuda, S.; Ito, Y. J. Org. Chem. 1998, 63, 3499-3503. Sunazuka, T.; Nagamitsu, T.; Tanaka H.; Omura, S.; Sprengeler, P. A.; Smith A. B. III. Tetrahedron Lett. 1993, 34, 4447-4448.
21. Some remarkable exceptions are: (a) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888. (b) Kuwano, R.; Okuda, S.; Ito, Y. J. Org. Chem. 1998, 63, 3499-3503. Sunazuka, T.; Nagamitsu, T.; Tanaka H.; Omura, S.; Sprengeler, P. A.; Smith A. B. III. Tetrahedron Lett. 1993, 34, 4447-4448.
22. Some remarkable exceptions are: (a) Evans, D. A.; Janey, J. M.; Magomedov, N.; Tedrow, J. S. Angew. Chem., Int. Ed. 2001, 40, 1884-1888. (b) Kuwano, R.; Okuda, S.; Ito, Y. J. Org. Chem. 1998, 63, 3499-3503. (c) Sunazuka, T.; Nagamitsu, T.; Tanaka H.; Omura, S.; Sprengeler, P. A.; Smith A. B. III. Tetrahedron Lett. 1993, 34, 4447-4448.
23. Bach, J.; Berenguer, R.; Garcia, J.; Loscertales, T.; Manzanal, J.; Vilarrasa, J. Tetrahedron Lett. 1997, 38, 1091-1094.
24. Amador, M.; Ariza, X.; Garcia, J.; Ortiz, J. Tetrahedron Lett. 2002, 43, 2691-2694.
25. 2, Lindlar catalyst, EtOAc), respectively.
26. For related cyclizations, see: (a) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1987, 28, 4837-4840. (b) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1990, 112, 1261-1263.
27. For related cyclizations, see: (a) Hayashi, T.; Yamamoto, A.; Ito, Y. Tetrahedron Lett. 1987, 28, 4837-4840. (b) Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1990, 112, 1261-1263.
28. The stereochemistry was assigned by NOE experiments and spectral data comparison with similar oxazolidinones: Kimura, M.; Tanaka, S.; Tamaru, Y. Bull. Chem. Soc. Jpn. 1995, 68, 1689-1705.
29. HPLC analysis of 6b derived from 2b (>99% ee) showed a single stereoisomer on a chiral column (Chiralcel OD-H, 9:1 hexane/2-propanol, 0.5 mL/min, t(-) = 12.7 min, t(+) = 16.3 min).
30. Acetonitrile improved the reaction rates and stereoselectivity.
31. Both π-allyl complexes are amenable to π-σ-π isomerization.
32. HPLC analysis of 7b on a Chiralcel OD-H column showed a single enantiomer (9:1 hexane/2-propanol, 0.5 mL/min, t(+) = 16.6 min, t(-) = 21.1 min).
33. Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567-569.
34. Carlsen, H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
35. Removal of tosyl group was successfully carried out in a number of oxazolidinones 12 or 13 in 65-94%: Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A. J.; Bank, S.; Closson, W. D.; Wriede, P. A. J. Am. Chem. Soc. 1967, 89, 5311-5312.
36. Spectral data fully agree with those reported: (a) Hale, K. J.; Manaviazar, S.; Delliser, V. M. Tetrahedron 1994, 50, 9181-9188. (b) Laïb, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709-1713.
37. Spectral data fully agree with those reported: (a) Hale, K. J.; Manaviazar, S.; Delliser, V. M. Tetrahedron 1994, 50, 9181-9188. (b) Laïb, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709-1713.