Regio- And stereoselective synthesis of alkyl allylic ethers via gold(l)-catalyzed intermodular hydroalkoxylation of allenes with alcohols

Organic Letters

Volumn 10, Issue 10, 2008, Pages 2079-2081

  Zhang, Zhibin ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE; ETHER DERIVATIVE; GOLD; ORGANOMETALLIC COMPOUND; SILVER;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; ALKENES; ALKYLATION; CATALYSIS; ETHERS; GOLD; HYDROXYLATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SILVER; STEREOISOMERISM;

EID: 46049088039     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800646h     Document Type: Article

References (41)

1. (a) Mitsunobu, O. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 6, pp 1 -31
2. (b) Feuer, H.; Hooz, J. In The Chemistry of the Ether Linkage; Patai, S., Ed.; Interscience Publishers: London, UK, 1967; pp 445-468.
3. (a) Evans, P. A.; Leahy, D. K. J. Am, Chem. Soc. 2002, 124, 7882.
4. (b) Evans, P. A.; Leahy, D. K.; Slieker, L. M. Tetrahedron: Asymmetry 2003, 14, 3613.
5. (c) Evans, P. A.; Leahy, D. K.; Andrews, W. J.; Uraguchi, D. Angew. Chem., Int. Ed. 2004, 43, 4788.
6. (a) Roberts. J. P.; Lee, C. Org. Lett. 2005, 7, 2679.
7. (b) Kim, H.; Lee, C. Org. Lett. 2002, 4, 4369.
8. (c) Kim. H.; Men, H.; Lee, C. J. Am. Chem. Soc. 2004, 126, 1336.
9. Trost, B. M.; McEachern, E. J.; Toste. F. D. J. Am. Chem. Soc. 1998, 120, 12702.
10. (a) Olsson, L.-L: Claesson, A. Synthesis 1979, 743.
11. (b) Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
12. Deutsch, C; Gockel, B.; Hoffmann-Röder, A.; Krause, N. Synlett 2007, 1790.
13. (a) Hamilton, G. L.; Kang, E. J.; Mba, M.; Toste, F. D. Science 2007, 317, 496.
14. (b) Volz, F.; Krause, N. Org. Biomol. Chem. 2007, 5, 1519.
15. (c) Hashmi, A. S. K.; Blanco. M. C; Fischer, D.; Bats, J. W. Eur. J. Org. Chem. 2006, 1387.
16. (d) Erdsak, J.; Krause, N. Synthesis 2007, 3741.
17. (e) Alcaide, B.; Almendros, P.; Martinez del Campo, T. Angew. Chem., Int. Ed. 2007, 46, 6684.
18. (a) Zhang, Z.; Liu. C; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer. R. A. J. Am. Chem. Soc. 2006, 128, 9066.
19. (b) Zhang, Z.; Widenhoefer, R. A. Angew. Chem. Ind. Ed. 2007, 46, 283.
20. (a) Hoffmann-Röder, A.; Krause, N. Org. Lett. 2001, 3, 2537.
21. (b) Gockel. B.; Krause, N. Org. Lett. 2006, 8, 4485.
22. Walkup, R. D.; Park. G. Tetrahedron Lett. 1987, 28, 1023.
23. Ma, S.; Yu, Z.; Wu, S. Tetrahedron 2001, 37, 1585.
24. Yu, X.; Seo. S.-Y.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 7244.
25. Patil, N. T.; Pahadi, N. K.; Yamamoto, Y. Can. J. Chem. 2005, 83, 569.
26. A BASF patent reported the Au(I)-catalyzed sequential addition of two molecules of methanol to the central carbon atom of allene to form 2,2-dimethoxypropane: Schulz. M.; Teles, J. H. (BASF AG), WO-A1 9721648, 1997; Chem. Abstr. 1997, 127, 121499.
27. For some related transformations, see:
28. (a) Utsunomiya, M,; Kawatsura, M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2003, 42, 5865.
29. (b) Nishina, N.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 3314.
30. (c) Nishina, N.; Yamamoto, Y. Synlett 2007, 1767.
31. (d) Kim, I. S.: Krische, M. J. Org. Lett. 2008, 10, 513.
32. Control experiments ruled out the presence of Ag(I) or acid-catalyzed hydroalkoxylation pathways (see the Supporting Information).
33. (a) Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004,126, 15978.
34. (b) Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148.
35. (c) Morita, N.; Krause, N. Eur. J. Org. Chem. 2006, 4634.
36. (a) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526.
37. (b) Zhang, J.; Yang. C.-G.; He, C. J. Am. Chem. Soc. 2006, 128, 1798.
38. (c) Hashmi. A. S. K.; Weyrauch, J. P.; Frey, W.; Bats, J. W. Org. Lett. 2004, 6, 4391.
39. (d) Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409.
40. Johnson, A.; Puddephatt, R. J. J. Chem. Soc, Dalton Trans. 1978, 980.
41. The intermediacy of III is further supported by the rapid (≤ 10min) racemization of (R)-12 (78% ee) at room temperature in the presence of (5)AuCl/AgOTf, presumably due to enhanced stabilization of the allylic cation by the conjugated phenyl group (see the Supporting Information).