Catalytic, asymmetric synthesis of 1,4-benzoxazinones: A remarkably enantioselective route to α-amino acid derivatives from o-benzoquinone imides

Angewandte Chemie - International Edition

Volumn 45, Issue 44, 2006, Pages 7398-7400

  Wolfer, Jamison ^a   Bekele, Tefsit ^a   Abraham, Ciby J ^a   Dogo Isonagie, Cajetan ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

Amino acids; Asymmetric catalysis; Benzoxazines; Benzoxazinones; Cycloaddition

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; CATALYSIS; SYNTHESIS (CHEMICAL);

ASYMMETRIC CATALYSIS; BENZOXAZINES; BENZOXAZINONES; CYCLOADDITION;

AROMATIC COMPOUNDS;

AMINO ACID; BENZOQUINONE DERIVATIVE; BENZOXAZINE DERIVATIVE; IMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINO ACIDS; BENZOQUINONES; BENZOXAZINES; CATALYSIS; IMIDES; MOLECULAR STRUCTURE;

EID: 33751218041     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602801     Document Type: Article

References (29)

1. Benzoxazinones are known as antitumor agents and protease inhibitors : a) S. K. Sengupta, D. H. Trites, M. S. Madhavarao, W. R. Beltz, J. Med. Chem. 1979, 22, 797;
2. b) R. L. Jarvest, S. C. Connor, J. G. Gorniak, L. J. Jennings, H. T. Serafinowska, A. West, Bioorg. Med. Chem. Lett. 1997, 7, 1733;
3. c) F. Bihel, J.-L. Kraus, Org. Biomol. Chem. 2003, 1, 793.
4. Benzoxazines are active as antioxidative neuroprotectants and antibiotics: a) M. Largeron, B. Lockhart, B. Pfeiffer, M.-B. Fleury, J. Med. Chem. 1999, 42, 5043;
5. b) Y.-G. Zhou, P.-Y. Yang, X.-W. Han, J. Org. Chem. 2005, 70, 1679;
6. c) J. Ilas, P. S. Anderluh, M. S. Delenc, D. Kikelj, Tetrahedron 2005, 61, 7325.
7. T. Bekele, M. H. Shah, J. Wolfer, C. J. Abraham, A. Weatherwax, T. Lectka, J. Am. Chem. Soc. 2006, 128, 1810.
8. For recent examples of asymmetric α-amino acid synthesis, see: a) T. Abellan, R. Chinchilla, N. Galindo, G. Guillena, C. Najera, J. M. Sansano, Eur. J. Org. Chem. 2000, 2689;
9. b) J. Kobayashi, M. Nakamura, Y. Mori, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 9192;
10. c) T. Belser, M. Stohr, A. Pfaltz, J. Am. Chem. Soc. 2005, 127, 8720.
11. K. Kacprzak, J. Gawronski, Synthesis 2001, 7, 961.
12. a) D. P. Huber, K. Stanek, A. Togni, Tetrahedron: Asymmetry 2006, 17, 658;
13. b) B. Mohar, J. Baudoux, J.-C. Plaquevent, D. Cahard, Angew. Chem. 2001, 113, 4666;
14. Angew. Chem. Int. Ed. 2001, 40, 4214.
15. P. Meffre, F. Le Goffic, Amino Acids 1996, 11, 313.
16. N2 substrates exist), or the Strecker reaction (that is, the conditions for the hydrolysis of the nitrite group can be harsh for 5g, 5h, and 5p).
17. V. P. Kukhar in Fluorine-Containing Amino Acids, Synthesis and Properties (Ed.: V. A. Soloshonok), Wiley, Chichester, 1995.
18. a) D. Ferraris, B. Young, T. Dudding, T. Lectka, J. Am. Chem. Soc. 1998, 120, 4548;
19. b) A. E. Taggi, A. M. Hafez, H. Wack, B. Young, W. J. Drury III, T. Lectka, J. Am. Chem. Soc. 2000, 122, 7831.
20. For a detailed study of o-quinone imide cycloadditions: K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, J. Am. Chem. Soc. 2002, 124, 2221.
21. 4 oxidation.
22. The opposite S enantiomer products can be made in comparable selectivity with benzoylquinine (BQ, 3b) as the catalyst.
23. Absolute configurations were determined by correlation to several known α-amino acid derivatives; the sense of induction observed was consistent with that obtained in other cinchona alkaloid catalyzed reactions (see Reference [10]).
24. K. F. Croom, K. L. Goa, Drugs 2003, 63, 2769.
25. P. Verma, S. Singh, D. K. Dikshit, R. Suprabhat, Synthesis 1987, 1, 68.
26. Reactions were quenched with a THF solution of the desired nucleophile at room temperature.
27. R. Adams, J. M. Stewart, J. Am. Chem. Soc. 1952, 74, 5876.
28. For an example of dearylation by using CAN, see: S. Kobayashi, J. Kobayashi, H. Ishiani, M. Ueno, Chem. Eur. J. 2002, 8, 4185.
29. For a review, see: L. A. Carpino, Acc. Chem. Res. 1987, 20, 401.