N,O-heterocycles as synthetic intermediates

Pure and Applied Chemistry

Volumn 80, Issue 4, 2008, Pages 681-685

  Bates, Roderick W ^a   Boonsombat, Jutatip ^a   Lu, Yongna ^a   Nemeth, Joseph A ^a   Sa Ei, Kanicha ^a   Song, Ping ^a   Cai, Melody Peiling ^a   Cranwell, Philippa B ^a   Winbush, SusAnn ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

Cyclization; Hydroxylamines; Isoxazolidines; Monomorine; Sakurai conditions; Sedamine; Tetrahydrooxazines

Indexed keywords

EID: 42449128839     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200880040681     Document Type: Conference Paper

References (20)

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4. (b) M. Tiecco, L. Testaferri, F. Marini, S. Sternativo, C. Santi, L. Bagnoli, A. Temperini. Tetrahedron: Asymmetry 12, 3053 (2001).
5. R. W. Bates, K. Sa-Ei. Org. Lett. 4, 4225 (2002).
6. For a discussion, see: R. W. Bates. Organic Synthesis using Transition Metals, Chap. 5, Academic Press, Sheffield (2000).
7. (a) E. Grochowski, J. Jurczak. Synthesis 682 (1976);
8. (b) N. I. Totah, S. L. Schreiber. J. Org. Chem. 56, 6255 (1991);
9. (c) H. Iwagami, M. Yatagai, M. Nakazawa, H. Orita, Y. Honda, T. Ohnuki, T. Yukawa. Bull. Chem. Soc. Jpn. 64, 175 (1991).
10. (a) R. W. Bates, J. Boonsombat. Org. Biomol. Chem. 3, 520 (2005);
11. for a review of the synthesis of sedum alkaloids, see: (b) R. W. Bates, K. Sa-Ei. Tetrahedron 58, 5957 (2002).
12. A serendipitously discovered reaction: (a) A. Claesson, C. Sahlberg, K. Luthman. Acta Chem. Scand. B 309 (1979);
13. (b) A. Claesson, L.-I. Olsson. Synthesis 743 (1979).
14. R. W. Bates, J. A. Nemeth, R. Snell. Synthesis. In press.
15. In contrast to Moody's experience, see: J. C. A. Hunt, P. Laurent, C. J. Moody. J. Chem. Soc, Perkin Trans. 1 2378 (2002).
16. R. W. Bates, R. Snell, S. Winbush. Synlett. In press.
17. R. W. Bates, P. Song. Unpublished results.
18. For a recent example, see: (a) S. S. Kinderman, R. de Gelder, J. H. van Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes. J. Am. Chem. Soc. 126, 4100 (2004);
19. the reactions of the corresponding O,O-acetals are well known: (b) P. A. Bartlett, W. S. Johnson, J. D. Elliott. J. Am. Chem. Soc. 105, 2088 (1983).
20. H. Sakurai. Pure Appl. Chem. 54, 1 (1982).