Directed hydrozirconation of homopropargylic alcohols

Tetrahedron

Volumn 64, Issue 29, 2008, Pages 6955-6960

  Liu, Xiaofeng ^a   Ready, Joseph M ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 BROMOPHENYL) 3 IODO 4 PHENYLBUT 3 EN 1 OL; 1 ETHOXY 2 IODOHEXADEC 1 EN 4 OL; 4 IODO 5 PHENYLPENT 4 EN 2 OL; 4 IODO 7 (4 METHOXYBENZYLOXY)HEPT 4 EN 2 OL; 4 IODO 7 (TRIISOPROPYLSILYLOXY)HEPT 4 EN 2 OL; 4 IODOPENTADEC 4 EN 5 OL; 7 IODOOCTADEC 7 EN 5 OL; 8 IODOOCTADEC 7 EN 5 OL; 9 (DIBENZYLAMINO) 4 IODONON 4 EN 2 OL; ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; IODINATION; ISOMERIZATION; METALLATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 44949175911     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.052     Document Type: Article

References (44)

1. Negishi E.-I. Acc. Chem. Res. 20 (1987) 65-72
2. Normant J.-F. Alkyne Carbocupration and Polyene Synthesis. In: Taylor R.J.K. (Ed). Organocopper Reagents (1994), IRL, Oxford, UK 237-256
3. Negishi E.-I., and Choueiry D. Reaction of Alkynes with Organometallic Reagents. In: Williams J.M.J. (Ed). Preparation of Alkenes (1996), Oxford University Press, Oxford, UK 137-155
4. Flynn A.B., and Ogilvie W.W. Chem. Rev. 107 (2007) 4698-4745
5. Eymery F., Iorga B., and Savignac P. Synthesis (2000) 185-213
6. Gilbert J.C., and Weerasooriya U. J. Org. Chem. 44 (1979) 4997-4998
7. Schwartz J., and Labinger J.A. Angew. Chem., Int. Ed. Engl. 88 (1976) 402-409
8. Negishi E., and Takahashi T. Synthesis (1988) 1-19
9. Wipf P., and Jahn H. Tetrahedron 52 (1996) 12853-12910
10. Wipf P., and Kendall C. Top. Organomet. Chem. 8 (2005) 1-25
11. Hart D.W., Blackburn T.F., and Schwartz J. J. Am. Chem. Soc. 97 (1975) 679-680
12. An exception:. Wang Y.D., Kimball G., Prashad A.S., and Wang Y. Tetrahedron Lett. 46 (2005) 8777-8780
13. Wipf P., Takahashi H., and Zhuang N. Pure Appl. Chem. 70 (1998) 1077-1082
14. Zhang D.H., and Ready J.M. J. Am. Chem. Soc. 129 (2007) 12088-12089
15. Under these conditions, internal propargylic alcohols are converted to allenes. Details will be reported separately.
16. Zhang D., and Ready J.M. J. Am. Chem. Soc. 128 (2006) 15050-15051
17. Snieckus V. Chem. Rev. 90 (1990) 879-933
18. Hoveyda A.H., Evans D.A., and Fu G.C. Chem. Rev. 93 (1993) 1307-1370
19. Fallis A.G., and Forgione P. Tetrahedron 57 (2001) 5899-5913
20. Non-directed hydrozirconation of homopropargylic alcohols:
21. Caddick S., Shanmugathasan S., Brasseur D., and Delisser V.M. Tetrahedron Lett. 38 (1997) 5735-5736
22. Kasatkin A., and Whitby R.J. J. Am. Chem. Soc. 121 (1999) 7039-7049
23. Dadboub M.J., Dabdoub V.B., and Baroni A.C.M. J. Am. Chem. Soc. 123 (2001) 9694-9695
24. Hoveyda A.H., Xu Z., Morken J.P., and Houri A.F. J. Am. Chem. Soc. 113 (1991) 8950-8952
25. Hoveyda A.H., Morken J.P., Houri A.F., and Xu Z. J. Am. Chem. Soc. 114 (1992) 6692-6697
26. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2793
27. Marshall J.A. J. Org. Chem. 72 (2007) 8153-8166
28. Yamaguchi M., and Hirao I. Tetrahedron Lett. 24 (1983) 391-394
29. Evans A.B., and Knight D.F. Tetrahedron Lett. 42 (2001) 6947-6948
30. Cis selective:. Tamao K., Maeda K., Tanaka T., and Ito Y. Tetrahedron Lett. 29 (1988) 6955-6956
31. Trans selective:
32. Denmark S.E., and Pan W. Org. Lett. 4 (2002) 4163-4166
33. Trost B.M., and Ball Z.T. J. Am. Chem. Soc. 127 (2005) 17644-17655
34. Ma S., Liu F., and Negishi E.-I. Tetrahedron Lett. 38 (1997) 3829-3832
35. Kluender, H. C.; Woessner, W. D.; Biddlecom, W. G. U.S. Patent 4,132,738, 1979.
36. Mura K., Wang D., Matsumoto Y., and Hosomi A. Org. Lett. 7 (2005) 503-505
37. Using 2 equiv Schwartz reagent under more concentrated reaction conditions led to incomplete conversion.
38. Commercial Schwartz reagent varies in purity. We purchased reagent from Strem and used it within 2 months without correcting for impurities.
39. Takaya H., Yamakawa M., and Mashima K. J. Chem. Soc., Chem. Commun. (1983) 1283-1284
40. Negishi E.-I. Acc. Chem. Res. 15 (1982) 340-348
41. Tucker C.E., Greve B., Klein W., and Knochel P. Organometallics 13 (1994) 94-101
42. Guan J., Kyle D.E., Gerena L., Zhang Q., Milhous W.K., and Lin A.J. J. Med. Chem. 45 (2002) 2741-2748
43. Compound 6 in. Woodward A.R., Burks H.E., Chan L.M., and Morken J.P. Org. Lett. 7 (2005) 5505-5507
44. Compounds 2c,d in. Luo F.-T., Wang M.-W., and Liu Y.-S. Heterocycles 43 (1996) 2725-2732