Diastereoselective synthesis of 2,6-imino-D-allonates from chromium carbene iminosugars

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3683-3684

  Klumpe, Markus ^a   Dötz, Karl Heinz ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Carbenes and carbenoids; Carbohydrates; Ketenes; Photochemistry

Indexed keywords

CHROMIUM DERIVATIVE;

ARTICLE; PHOTOLYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032575198     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00620-0     Document Type: Article

References (18)

1. [1] Organotransition Metal Modified Sugars, part 9; for part 8, see: Dötz, K. H.; Weyershausen, B.; Nieger, M. Organometallics, submitted for publication. Review: Dötz, K. H.; Ehlenz, R. Chem. Eur. J. 1997, 3, 1751.
2. [1] Organotransition Metal Modified Sugars, part 9; for part 8, see: Dötz, K. H.; Weyershausen, B.; Nieger, M. Organometallics, submitted for publication. Review: Dötz, K. H.; Ehlenz, R. Chem. Eur. J. 1997, 3, 1751.
3. [2] Reviews: a) Dötz, K. H. Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587;
4. [2] Reviews: a) Dötz, K. H. Angew. Chem. 1984, 96, 573; Angew. Chem. Int. Ed. Engl. 1984, 23, 587;
5. b) Wulff, W. D. in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone, G. Wilkinson, Pergamon Press, New York, 1995, vol. 12, 470.
6. [3] Reviews: a) Hegedus, L. S. in Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone, G. Wilkinson, Pergamon Press, New York, 1995, vol. 12, 549;
7. b) Hegedus, L. S. Tetrahedron 1997, 53, 4105.
8. [4] For the preparation of 1,4-iminofuranosylidene complexes see: Dötz, K. H.; Haase, W. C.; Klumpe, M.; Nieger, M. J. Chem. Soc. Chem. Commun. 1997, 1217.
9. [5] For the synthesis of 2,6-imino-D-aldonic acids in L-gulo, L-ido-, D-manno or L-galacto-configuration, see: a) Bashyal, B. P.; Chow, H.-F.; Fleet, G. W. J. Tetrahedron Lett. 1986, 27, 3205;
10. b) Bashyal, B. P.; Chow, H.-F.; Fellows, F. E.; Fleet, G. W. J. Tetrahedron 1987, 43, 415;
11. c) Fleet, G. W. J.; Fellows, F. E.; Smith, P. W. Tetrahedron 1987, 43, 979;
12. d) Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327;
13. e) Tong, M. K.; Blumenthal, E. M.; Ganem, B. Tetrahedron Lett. 1990, 31, 1683;
14. f) Park, K. H.; Yoon, Y. J.; Lee, S. G. J. Chem. Soc. Perkin Trans. I 1994, 2621.
15. [6] a) Imwinkelried, R.; Hegedus, L. S. Organometallics 1988, 7, 702;
16. b) Schwindt, M. A.; Lejon, T.; Hegedus, L. S. Organometallics 1990, 9, 2814.
17. [7] The configuration was confirmed by NOE experiments.
18. 5 calc.: 299.1732 found: 299.1741.