Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination

Tetrahedron Letters

Volumn 49, Issue 33, 2008, Pages 4908-4911

  Nishina, Naoko ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alcohol; Allene; Allylic ether; Chirality transfer; Gold catalysis; Gold chloride; Hydroalkoxylation; Silver triflate

Indexed keywords

ALCOHOL; ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; ETHER DERIVATIVE; GOLD; GOLD CHLORIDE; SILVER;

AMINATION; ARTICLE; CATALYST; CHEMICAL REACTION; HYDROALKOXYLATION; HYDROAMINATION; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS;

EID: 46049101430     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.152     Document Type: Article

References (57)

1. For recent reviews of catalytic hydroalkoxylation, see:. Tani K., and Kataoka Y. In: Togni A., and Grützmacher H. (Eds). Catalytic Heterofunctionalization (2001), Wiley-VCH, Weinheim 171-216
2. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079-3159
3. Tzalis D., Koradin C., and Knochel P. Tetrahedron Lett. 40 (1999) 6193-6195
4. For recent examples of Lewis acidic transition metal catalyzed hydroalkoxylation, see:. Qian H., Han X., and Widenhoefer R.A. J. Am. Chem. Soc. 126 (2004) 9536-9537
5. Patil N.T., Pahadi N.K., and Yamamoto Y. Can. J. Chem. 83 (2005) 569-573
6. Oe Y., Ohta T., and Ito Y. Synlett (2005) 179-181
7. Matsukawa Y., Mizukado J., Quan H., Tamura M., and Sekiya A. Angew. Chem., Int. Ed. 44 (2005) 1128-1130
8. Coulombel L., Favier I., and Duñach E. Chem. Commun. (2005) 2286-2288
9. Hirabayashi T., Okimoto Y., Saito A., Morita M., Sakaguchi S., and Ishii Y. Tetrahedron 62 (2006) 2231-2234
10. Gligorich K.M., Schultz M.J., and Sigman M.S. J. Am. Chem. Soc. 128 (2006) 2794-2795
11. Coulombel L., Rajzmann M., Pons J.-M., Olivero S., and Duñach E. Chem. Eur. J. 12 (2006) 6356-6365
12. Yu X., Seo S.Y., and Marks T.J. J. Am. Chem. Soc. 129 (2007) 7244-7245
13. Lemechko P., Grau F., Antoniotti S., and Duñach E. Tetrahedron Lett. 48 (2007) 5731-5734
14. For recent examples of gold-catalyzed intramolecular hydroalkoxylation, see:. Hoffmann-Röder A., and Krause N. Org. Lett. 16 (2001) 2537-2538
15. Liu Y., Song F., Song Z., Liu M., and Yan B. Org. Lett. 7 (2005) 5409-5412
16. Hashmi A.S.K., Blanco M.C., Fischer D., and Bats J.W. Eur. J. Org. Chem. (2006) 1387-1389
17. Belting V., and Krause N. Org. Lett. 8 (2006) 4489-4492
18. Liu B., and De Brabander J.K. Org. Lett. 8 (2006) 4907-4910
19. Zhang Z., Liu C., Kinder R.E., Han X., Qian H., and Widenhoefer R.A. J. Am. Chem. Soc. 128 (2006) 9066-9073
20. Zhang Z., and Widenhoefer R.A. Angew. Chem., Int. Ed. 46 (2007) 283-285
21. Alcaide B., Almendros P., and del Campo T.M. Angew. Chem., Int. Ed. 46 (2007) 6684-6687
22. Deutsch C., Gockel B., Hoffmann-Röder A., and Krause N. Synlett (2007) 1790-1794
23. Volz F., and Krause N. Org. Biomol. Chem. 5 (2007) 1519-1521
24. Hamilton G.L., Kang E.J., Mba M., and Toste F.D. Science 317 (2007) 496-499
25. Erdsack J., and Krause N. Synthesis (2007) 3741-3750
26. Norman R.O.C., Parr W.J.E., and Thomas C.B. J. Chem. Soc., Perkin Trans. 1 (1976) 1983-1987
27. For selected reviews of hydration, see:. Oestreich M. In: Brückner R. (Ed). Science of Synthesis Vol. 25 (2006), Thieme, Stuttgart 199-212
28. Hintermann L., and Labonne A. Synthesis (2007) 1121-1150
29. Beller M., Seayad J., Tillack A., and Jiao H. Angew. Chem., Int. Ed. 43 (2004) 3368-3398
30. For selected recent reviews of gold catalysis, see:. Widenhoefer R.A., and Han X. Eur. J. Org. Chem. (2006) 4555-4563
31. Hashmi A.S.K., and Hutchings G.J. Angew. Chem., Int. Ed. 45 (2006) 7896-7936
32. Zhang L., Sun J., and Kozmin S.A. Adv. Synth. Catal. 348 (2006) 2271-2296
33. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180-3211
34. Fürstner A., and Davies P.W. Angew. Chem., Int. Ed. 46 (2007) 3410-3449
35. Gorin D.J., and Toste F.D. Nature 446 (2007) 395-403
36. Patil, N. T.; Yamamoto, Y. Arkivoc 2007, v, 6-19.
37. For examples of improved hydration in gold catalysis, see:. Fukuda Y., and Utimoto K. Bull. Chem. Soc. Jpn. 64 (1991) 2013-2015
38. Mizushima E., Sato K., Hayashi T., and Tanaka M. Angew. Chem., Int. Ed. 41 (2002) 4563-4565
39. Casado R., Contel M., Laguna M., Romero P., and Sanz S. J. Am. Chem. Soc. 125 (2003) 11925-11935
40. Roembke P., Schmidbaur H., Cronje S., and Raubenheimer H. J. Mol. Catal. A: Chem. 212 (2004) 35-42
41. Fukuda Y., and Utimoto K. J. Org. Chem. 56 (1991) 3729-3731
42. Fukuda, Y.; Utimoto, K. JP Patent 04095039, 1992; Chem. Abstr. 1992, 117, 191330.
43. Schulz, M.; Teles, J. H. WO Patent 9721648, 1997; Chem. Abstr. 1997, 127, 121499.
44. Teles J.H., Brode S., and Chabanas M. Angew. Chem., Int. Ed. 37 (1998) 1415-1418
45. Yang C.-G., and He C. J. Am. Chem. Soc. 127 (2005) 6966-6967
46. Tian G.-Q., and Shi M. Org. Lett. 9 (2007) 4917-4920
47. Nishina N., and Yamamoto Y. Angew. Chem., Int. Ed. 45 (2006) 3314-3317
48. Nishina N., and Yamamoto Y. Synlett (2007) 1767-1770
49. Nishina, N. Ph.D. Dissertation, Tohoku University, 2007.
50. The reaction was very exothermic, and resulted in the formation of a complex mixture of products. The corresponding allylic ether was not detected by GC-MS and NMR. To make the reaction conditions milder, the hydroalkoxylation in dilute toluene was carried out, but the corresponding product was not detected.
51. Addition of a reactive alcohol, such as phenol can be catalyzed by a Brønsted acid, see:. Rosenfeld D.C., Shekhar S., Takeymiya A., Utsunomiya M., and Hartwig J.F. Org. Lett. 8 (2006) 4179-4182
52. Hashmi A.S.K. Angew. Chem., Int. Ed. 39 (2000) 3590-3593
53. Hashmi A.S.K. In: Schmalz H.-G., and Wirth T. (Eds). Organic Synthesis Highlights V (2003), Wiley-VCH, Weinheim 56-67
54. For examples of gold-mediated racemization of allenes, see:. Sherry B.D., and Toste F.D. J. Am. Chem. Soc. 126 (2004) 15978-15979
55. Zhang Z., Bender C.F., and Widenhoefer R.A. J. Am. Chem. Soc. 129 (2007) 14148-14149
56. Roithová J., Hrušák J., Schröder D., and Schwarz H. Inorg. Chim. Acta 358 (2005) 4287-4292
57. Quite recently, the gold-catalyzed intermolecular hydroalkoxylation of allenes with alcohols, which is very similar with the present paper, has been published;. Zhang Z., and Widenhoefer R.A. Org. Lett. 10 (2008) 2079-2081