Primary amides. A general nitrogen source for catalytic asymmetric aminohydroxylation of olefins

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2221-2223

  Demko, Zachary P ^a   Bartsch, Michael ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; ALKENE; AMIDE; CINNAMIC ACID DERIVATIVE; N BROMOACETAMIDE; N-BROMOACETAMIDE; NITROGEN; THIOUREA;

ARTICLE; CHEMISTRY; HYDROXYLATION; METABOLISM; STEREOISOMERISM;

ACETAMIDES; ALKENES; AMIDES; CINNAMATES; HYDROXYLATION; NITROGEN; STEREOISOMERISM; THIOUREA;

EID: 0034720949     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000098m     Document Type: Article

References (28)

1. The Merck Index, 12th ed.; Chapman & Hall: New York, 1996. Shaw, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 7, pp 397-429.
2. The Merck Index, 12th ed.; Chapman & Hall: New York, 1996. Shaw, G. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 7, pp 397-429.
3. Li, G.; Chang, H-.T.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454.
4. (b) Li, G.; Sharpless, K. B. Acta Chem. Scand. 1996, 50, 649-651.
5. (a) Rudolph, J.; Sennhenn, P. C.; Vlaar, C. P.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2810-2813.
6. (b) Reddy, K. L.; Dress, K. R.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 3667-3670.
7. (c) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Fine Chemicals and Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: New York, 1998; Vol. 2., pp 243-260.
8. (d) Schlingloff, G.; Sharpless, K. B. In Asymmetric Oxidation Reactions: A Practical Approach; Katsuki, T., Ed.; Oxford University: Oxford, U.K.; in press.
9. Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813-2817.
10. (a) Goossen, L. J.; Liu, H.; Dress, K. R.; Sharpless, K. B. Angew. Chem., Int. Ed. 1999, 38, 1080-1083.
11. (b) Dress, K. R.; Goossen, L. J.; Liu, H.; Jerina, D. M.; Sharpless, K. B. Tetrahedron Lett. 1998, 39, 7669-7672.
12. Bruncko, M.; Schlingloff, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1483-1486.
13. (a) Park, J. D.; Gerjovich, H. J.; Lycan, W. R.; Lacher, J. R. J. Am. Chem. Soc. 1952, 74, 2189-2192.
14. (b) Bachard, C.; Driguez, H.; Paton, J. M.; Touchard, D.; Lessard, J. J. Org. Chem. 1974, 39, 3136-3138.
15. (c) Kajigaeshi, S.; Nakagawa, T.; Fujisaki, S. Chem. Lett. 1984, 2045-2046.
16. The exceptions are the three commercially available halogenated nitrogen salts, (N-chloro,N-sodio-p-toluenesulfonamide, N-chloro,N-sodio-benzene sulfonamide, and N-bromoacetamide), and the recently reported N-bromobenzamide (see: Song, C. E.; Oh, C. R.; Roh, E. J.; Lee, S.; Choi, J. H. Tetrahedron Asymmetry 1999, 10, 671-674).
17. Wallis, E. S.; Lane, J. F. Org. React. 1967, 3, 267-306.
18. Gottardi, W. Monatsh. Chem. 1975, 106, 611-623.
19. 2 (63.9 g, 400 mmol). After the bromine is dissolved, the solution is placed in the refrigerator overnight. The solution is then filtered, and the filtrate is dried in vacuo to yield DBI as a white powder. Taken from: Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Ed.: Wiley: West Sussex, 1995; p 1560.
20. 1H NMR analysis was shown to be 99% N-bromo chloroacetamide and 1% starting material. N-Bromoamides were stored under vacuum.
21. 2 afforded 2a as a white powder (1.38 g., 94%, 21:1 regioisomeric ratio).
22. 2PHAL ligand is used, the enantioselectivity was also 95%, with the (25,3R) product predominating.
23. (a) Masaki, M.; Kitahara, T.; Kurita, H.; Ohta, M. J. Am. Chem. Soc. 1968, 90, 4508-4509.
24. (b) Steglich, W.; Batz, H. G. Angew. Chem., Int. Ed. Engl. 1971, 10, 75-76.
25. (c) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 1991; pp 352-353.
26. Kolb, H. C.; Andresson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1994, 116, 1278-1291.
27. Use of 10 mol % catalyst and ligand greatly increased both the reliability and the selectivity of the reaction. It also was noted that when the pH of the solution was above 9, or above 8 for electron-deficient amides, no reaction was observed.
28. Chang, H.-T. Ph.D. Thesis, The Scripps Research Institute (US), 1996.