Regio- and stereocontrolled dimerisation of allenic alcohols via introduction of an acetoxy group using ruthenium catalysis

Tetrahedron Letters

Volumn 44, Issue 38, 2003, Pages 7151-7154

  Yoshida, Masahiro ^a   Gotou, Takahiro ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; AMINE; COPPER ACETATE; DIMER; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIMERIZATION; REACTION OPTIMIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 0042009415     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01807-0     Document Type: Article

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22. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
23. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
24. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
25. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
26. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
27. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
28. For other transition metal-catalysed dimerisations of allenes, see: (a) Oh, C. H.; Yoo, H. S.; Jung, S. H. Chem. Lett. 2001, 1288; (b) Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776; (c) Arisawa, M.; Sugihara, T.; Yamaguchi, M. Chem. Commun. 1998, 2615; (d) Hideura, D.; Urabe, H.; Sato, F. Chem. Commun. 1998, 271; (e) Pasto, D. J.; Huang, N.-Z. ; Eigenbrot, C. W. J. Am. Chem. Soc. 1985, 122, 3107; (f) Pasto, D. J.; Huang, N.-Z. Organometallics 1995, 14, 2565; (g) Inoue, Y.; Ohtsuka, Y.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 3345; (h) Coulson, D. R. J. Org. Chem. 1973, 38, 1483; (i) Englert, M.; Jolly, P. W.; Wilke, G.; Englert, M.; Jolly, P. W.; Wilke, G. Angew. Chem., Int. Ed. 1972, 11, 136.
29. For review: Trost B.M., Pinkerton A.B. Chem. Rev. 101:2001;2067. and references cited therein.
30. A dimerised ruthenium complex of allene is reported: Lewandos G.S., Doherty N.M., Knox S.A.R., Macpherson K.A., Orpen A.G. Polyhedron. 7:1988;837.
31. Yoshida M., Sugimoto K., Ihara M. Tetrahedron Lett. 42:2001;3877.
32. Ruthenium-catalysed reaction of alkynes with carboxylic acids has been reported: see Ref. 1e.
33. Gill T.B., Mann K.R. Organometallics. 1:1982;485.
34. 2), found 276.2117.
35. This type of dimerisation has been reported using a stoichiometric amount of titanium complex, see Ref. 4d.
36. 1H NMR integration of deuterised methylene signals (δ 2.24 for 3a -d, δ 2.26 for 3a, δ 2.21 for 3c -d, δ 2.23 for 3c ).
37. Structure of 12 was determined by COSY, NOESY and C-H COSY.
38. This type of dimerisation has been reported using palladium complex, see Ref. 4c.