Catalytic aminohydroxylation using adenine-derivatives as the nitrogen source

Tetrahedron Letters

Volumn 39, Issue 42, 1998, Pages 7669-7672

  Dress, K Ruprecht ^a   Gooßen, Lukas J ^a   Liu, Hong ^a   Jerina, Donald M ^b   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE DERIVATIVE; ALKENE DERIVATIVE; OSMIUM;

AMINATION; ARTICLE; CATALYSIS; HYDROXYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032532224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01716-X     Document Type: Article

References (17)

1. 1. (a) The Merck Index; Chapman & Hall: New York, 1996; 12th Ed.
2. (b) Shaw, G. Bicyclic 5-6 System: Purines. In Comprehensive Heterocyclic Chemistry 11; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 7, pp. 397-429.
3. 2. Lakshman, M. K.; Yeh, H. J. C.; Yagi, H.; Jerina, D. M. Tetrahedron Lett. 1992, 33, 7121-7124. Kim, S. J.; Harris, C. M.; Jung, K.-Y.; Koreeda, M.; Harris, T. M. Tetrahedron Lett. 1991, 32, 6073-6076. Kiselyov, A. S.; Steinbrecher, T.; Harvey, R. G. J. Org. Chem. 1995, 60, 6129-6134.
4. 2. Lakshman, M. K.; Yeh, H. J. C.; Yagi, H.; Jerina, D. M. Tetrahedron Lett. 1992, 33, 7121-7124. Kim, S. J.; Harris, C. M.; Jung, K.-Y.; Koreeda, M.; Harris, T. M. Tetrahedron Lett. 1991, 32, 6073-6076. Kiselyov, A. S.; Steinbrecher, T.; Harvey, R. G. J. Org. Chem. 1995, 60, 6129-6134.
5. 2. Lakshman, M. K.; Yeh, H. J. C.; Yagi, H.; Jerina, D. M. Tetrahedron Lett. 1992, 33, 7121-7124. Kim, S. J.; Harris, C. M.; Jung, K.-Y.; Koreeda, M.; Harris, T. M. Tetrahedron Lett. 1991, 32, 6073-6076. Kiselyov, A. S.; Steinbrecher, T.; Harvey, R. G. J. Org. Chem. 1995, 60, 6129-6134.
6. 3. Pilcher, A. S.; Yagi, H.; Jerina, D. J. J. Am. Chem. Soc. 1998, 120, 3520-3521.
7. 4. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454.
8. (b) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2810-2813.
9. (c) Schlinghoff, G.; Sharpless, K. B. Asymmetric Aminohydroxylation. In Asymmetric Oxidation Reactions: A practical Approach; Katsuki, T., Ed.; Oxford University Press: Oxford, 1998; in press.
10. (d) Kolb, H. C.; Sharpless, K. B. Asymmetric Aminohydroxylation. In Transition Metals for Fine Chemicals and Organic Synthesis; Beller, M.; Bolm, C., eds.; Wiley-VCH: New York, 1998; in press.
11. 5. (a) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1996, 35, 2813-2815.
12. (b) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207-1217.
13. 6. Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1997, 36, 1483-1486.
14. 7. Sharpless, K. B.; Gooßen, L. G.; Liu, H.; Dress, K. R. publication in preparation.
15. 8. The regiochemistry of the products were confirmed by variable temperature 2D NMR studies.
16. 9. Verenikina, G.; Chauser, E. G.; Yurkevich, A. M. Zh. Obshch. Khim. 1971, 41, 1630-1632.
17. 10. For maximum reliability on small scale, a high osmium catalyst concentration (10 %) is recommended in these reactions. In most cases however, it was possible to reduce the catalyst content to 3 % without significant yield loss. (for compound 14: 76 % yield with 10 % catalyst, 74 % with 5 %, and 72 % with 3 %). It is also usually possible to reduce the excess of the chloramine salt of the adenine-derivative to two equivalents. At room temperature, for some substrates relatively long reaction times were required so that the reactions are best performed at 40 - 50 °C.