Segregation of separate steps in chromium-catalyzed reactions for convenience and mechanistic analysis

Organic Letters

Volumn 2, Issue 5, 2000, Pages 691-693

  Hari, Anitha ^a   Miller, Benjamin L ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

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[No Author keywords available]

Indexed keywords

EID: 0005978689     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0055364     Document Type: Article

References (23)

1. (a) Kautsky, H.; Hirsch, A.; Flesch, W. Chem. Ber. 1935, 68, 152-162.
2. (b) Kautsky, H. Trans. Faraday Soc. 1939, 35, 216-219.
3. (a) Rebek, J., Jr.; Gaviña, F.; Navarro, C. J. Am. Chem. Soc. 1978, 100, 8113-8117.
4. (b) Rebek, J., Jr. Tetrahedron 1979, 55, 723-731.
5. Parlow, J. J. Tetrahedron Lett. 1995, 36, 1395-1396.
6. Hari, A.; Miller, B. L. Angew. Chem., Int. Ed. 1999, 38, 2777-2779.
7. (a) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349-12357.
8. (b) Fürstner, A. Chem. Eur. J. 1998, 4, 567-570.
9. (a) Okude, Y.; Hirano, S.; Hiyama, T.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 3179-3181.
10. (b) Hiyama, T.; Okude, Y.; Kimura, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1982, 55, 561-568.
11. (c) Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281-5284.
12. Boeckman, R. K., Jr.; Hudack, R. A., Jr. J. Org. Chem. 1998, 63, 3524-3525.
13. (a) Takai, K.; Nitta, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 5263-5266.
14. (b) Fujimura, O.; Takai, K.; Utimoto, K. J. Org. Chem. 1990, 55, 1705-1706.
15. (c) Takai, K.; Kataoka, Y.; Utimoto, K. Tetrahedron Lett. 1989, 30, 4389-4392.
16. 2.
17. The procedure for the reduction employing Zn was essentially identical to the recycle test employing Mn; the reactor was charged with 2.1 g (33 mmol) of Zn prior to the first reduction cycle.
18. Sylvain, C.; Wagner, A.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 1043-1044.
19. A reactor (Figure 1) containing 1.9 g (35 mmol) of Mn was prepared as described previously. The Wang resin-bound aldehyde (50 mg, initial resin loading 0.7 mmol/g) was introduced to the reactor, followed by dry DMF, chromium chloride (1 mg, 0.008 mmol, 0.25 equiv), and TMS-Cl (67 μL, 0.528 mmol, 16 equiv). Allyl bromide (16.9 mg, 0.132 mmol, 4 equiv) was then added, and the reaction was shaken overnight at room temperature on a Burrell wrist-action shaker. Cleavage of the product was as described previously.
20. For reviews of applications of chromium in organic synthesis, see: (a) Fürstner, A. Chem. Rev. 1999, 99, 991-1045.
21. (b) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1-36.
22. (c) Ho, T.-L. Synthesis 1979, 1-20.
23. (d) Hanson, J. R.; Premuzic, E. Angew. Chem., Int. Ed. Engl. 1968, 7, 247-252.