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Volumn , Issue 8, 2008, Pages 1105-1124

Ruthenium-catalyzed isomerizations of allylic and propargylic alcohols in aqueous and organic media: Applications in synthesis

Author keywords

Alcohols; Homogeneous catalysis; Isomerizations; Ruthenium; Tandem reactions

Indexed keywords

ALCOHOL; ALLYL ALCOHOL; CARBONYL DERIVATIVE; RUTHENIUM;

EID: 44349092408     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072593     Document Type: Review
Times cited : (179)

References (136)
  • 1
    • 0026418434 scopus 로고
    • (a) Trost, B. M. Science 1991, 254, 1471.
    • (1991) Science , vol.254 , pp. 1471
    • Trost, B.M.1
  • 5
    • 0000677232 scopus 로고
    • (a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
    • (1993) Chem. Rev , vol.93 , pp. 2023
    • Li, C.-J.1
  • 9
    • 24044470646 scopus 로고    scopus 로고
    • (e) Li, C.-J. Chem. Rev. 2005, 105, 3095.
    • (2005) Chem. Rev , vol.105 , pp. 3095
    • Li, C.-J.1
  • 13
    • 44349140943 scopus 로고    scopus 로고
    • Organic Reactions in Water; Lindström, U. M., Ed.; Blackwell: Oxford, 2007.
    • (i) Organic Reactions in Water; Lindström, U. M., Ed.; Blackwell: Oxford, 2007.
  • 20
    • 17844369291 scopus 로고    scopus 로고
    • Murahashi, S.-I, Ed, Wiley-VCH: Weinheim
    • (f) Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, 2004.
    • (2004) Ruthenium in Organic Synthesis
  • 21
    • 15744379429 scopus 로고    scopus 로고
    • Bruneau, C, Dixneuf, P. H, Eds, Springer: Berlin
    • (g) Ruthenium Catalysts and Fine Chemistry; Bruneau, C.; Dixneuf, P. H., Eds.; Springer: Berlin, 2004.
    • (2004) Ruthenium Catalysts and Fine Chemistry
  • 22
    • 33645971054 scopus 로고    scopus 로고
    • For a thematic issue devoted to this topic, see: (h) Curr. Org. Chem. 2006, 10, 113-225.
    • For a thematic issue devoted to this topic, see: (h) Curr. Org. Chem. 2006, 10, 113-225.
  • 33
    • 0036569365 scopus 로고    scopus 로고
    • For reviews on the catalytic isomerization of allylic alcohols, see: a
    • For reviews on the catalytic isomerization of allylic alcohols, see: (a) van der Drift, R. C.; Bouwman, E.; Drent, E. J. Organomet. Chem. 2002, 650, 1.
    • (2002) J. Organomet. Chem , vol.650 , pp. 1
    • van der Drift, R.C.1    Bouwman, E.2    Drent, E.3
  • 35
    • 0000965591 scopus 로고    scopus 로고
    • 2 (OTs = p-toluenesulfonate) had proven to be an active catalyst for the isomerization of allylic alcohols and ethers in pure aqueous solution, see: (a) McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611.
    • 2 (OTs = p-toluenesulfonate) had proven to be an active catalyst for the isomerization of allylic alcohols and ethers in pure aqueous solution, see: (a) McGrath, D. V.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1991, 113, 3611.
  • 38
    • 85153009425 scopus 로고    scopus 로고
    • In addition, the catalytic systems mer, RuCl3(DMSO, phen, DMSO, dimethyl sulfoxide, phen, 1,10-phenanthroline),cis,cis-[RuCl2(DMSO)2(phen, and [Ru(acac)3]/phen/ PTSA (acac, acetylacetonate, PTSA, p-toluenesulfonic acid) had also been used for the isomerization of allylic alcohols in monophasic water/organic solvent mixtures, see: (d) van der Drift, R. C, Sprengers, J. W, Bouwman, E, Mul, W. P, Kooijman, H, Spek, A. L, Drent, E. Eur. J. Inorg. Chem. 2002, 2147
    • 3]/phen/ PTSA (acac = acetylacetonate, PTSA = p-toluenesulfonic acid) had also been used for the isomerization of allylic alcohols in monophasic water/organic solvent mixtures, see: (d) van der Drift, R. C.; Sprengers, J. W.; Bouwman, E.; Mul, W. P.; Kooijman, H.; Spek, A. L.; Drent, E. Eur. J. Inorg. Chem. 2002, 2147.
  • 48
    • 0004244329 scopus 로고    scopus 로고
    • Horváth, I. T, Joó, F, Eds, Kluwer: Dodrecht
    • (f) Aqueous Organometallic Catalysis; Horváth, I. T.; Joó, F., Eds.; Kluwer: Dodrecht, 2001.
    • (2001) Aqueous Organometallic Catalysis
  • 50
    • 44349085747 scopus 로고    scopus 로고
    • Thematic issues of journals have been devoted to the catalytic applications of water-soluble organometallic compounds, see: (a) J. Mol. Catal. A: Chem. 1997, 116, 1-316
    • Thematic issues of journals have been devoted to the catalytic applications of water-soluble organometallic compounds, see: (a) J. Mol. Catal. A: Chem. 1997, 116, 1-316.
  • 51
    • 0000316620 scopus 로고    scopus 로고
    • (b) Catalysis Today 1998, 42, 371-478.
    • (1998) Catalysis Today , vol.42 , pp. 371-478
  • 52
    • 85164466917 scopus 로고    scopus 로고
    • (c) Adv. Synth. Catal. 2002, 344, 219-451.
    • (2002) Adv. Synth. Catal , vol.344 , pp. 219-451
  • 53
    • 44349114182 scopus 로고    scopus 로고
    • A short account covering the synthesis and catalytic applications in water of platinum metals containing this ligand is available, see: Pringle, P. G, Smith, M. B. Platinum Met. Rev. 1990, 34, 74
    • A short account covering the synthesis and catalytic applications in water of platinum metals containing this ligand is available, see: Pringle, P. G.; Smith, M. B. Platinum Met. Rev. 1990, 34, 74.
  • 63
    • 0000614702 scopus 로고    scopus 로고
    • 3) as catalysts, see: (a) Slugovc, C.; Rüba, E.; Schmid, R.; Kirchner, K. Organometallics 1999, 18, 4230.
    • 3) as catalysts, see: (a) Slugovc, C.; Rüba, E.; Schmid, R.; Kirchner, K. Organometallics 1999, 18, 4230.
  • 64
    • 44349181208 scopus 로고    scopus 로고
    • 3,
    • 3,
  • 77
    • 44349193035 scopus 로고    scopus 로고
    • Some other catalytic systems are also able to isomerize trisubstituted allylic alcohols, although they require higher temperatures (70-120°C) and/or longer reaction times: (a) See also ref. 16
    • Some other catalytic systems are also able to isomerize trisubstituted allylic alcohols, although they require higher temperatures (70-120°C) and/or longer reaction times: (a) See also ref. 16
  • 78
    • 44349187075 scopus 로고    scopus 로고
    • See also ref. 21
    • (b) See also ref. 21
  • 82
    • 33749139719 scopus 로고    scopus 로고
    • and references cited therein. For example, see
    • For example, see: Morrill, C.; Beutner, G. L.; Grubbs, R. H. J. Org. Chem. 2006, 71, 7813; and references cited therein.
    • (2006) J. Org. Chem , vol.71 , pp. 7813
    • Morrill, C.1    Beutner, G.L.2    Grubbs, R.H.3
  • 93
    • 44349084547 scopus 로고    scopus 로고
    • See also ref. 30d
    • (f) See also ref. 30d
  • 99
    • 0000894377 scopus 로고
    • For a review on the Meyer-Schuster and Rupe rearrangements, see
    • For a review on the Meyer-Schuster and Rupe rearrangements, see: Swaminathan, S.; Narayanan, K. V. Chem. Rev. 1971, 71, 429.
    • (1971) Chem. Rev , vol.71 , pp. 429
    • Swaminathan, S.1    Narayanan, K.V.2
  • 115
    • 33748928795 scopus 로고    scopus 로고
    • We note that gold-catalyzed isomerizations of internal alkynols operating under remarkably mild conditions (CH2Cl2, r.t, have recently been described, see: (a) Engel, D. A, Dudley, G. B. Org. Lett. 2006, 8, 4027
    • 2, r.t.) have recently been described, see: (a) Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027.
  • 120
    • 5244284889 scopus 로고
    • For reviews on the chemistry of transition-metal-vinylidene and -allenylidene complexes, see: a
    • For reviews on the chemistry of transition-metal-vinylidene and -allenylidene complexes, see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
    • (1991) Chem. Rev , vol.91 , pp. 197
    • Bruce, M.I.1
  • 121
  • 124
    • 5344269459 scopus 로고    scopus 로고
    • For a special issue devoted to the chemistry of vinylidenes, allenylidenes, and related metallacumulenes, see: e
    • For a special issue devoted to the chemistry of vinylidenes, allenylidenes, and related metallacumulenes, see: (e) Coord. Chem. Rev. 2004, 248, 1531-1715.
    • (2004) Coord. Chem. Rev , vol.248 , pp. 1531-1715
  • 130
    • 0012720437 scopus 로고    scopus 로고
    • 4] via cyclization of the initially formed enal, see: Shvo, Y.; Blum, Y.; Reshef, D. J. Organomet. Chem. 1982, 238, C79.
    • 4] via cyclization of the initially formed enal, see: Shvo, Y.; Blum, Y.; Reshef, D. J. Organomet. Chem. 1982, 238, C79.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.