메뉴 건너뛰기




Volumn , Issue 19, 2006, Pages 4367-4378

Borrowing hydrogen: Indirect "Wittig" olefination for the formation of C-C bonds from alcohols

Author keywords

Dehydrogenation; Domino reactions; Iridium; Transfer hydrogenation; Wittig reactions

Indexed keywords


EID: 33749429963     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600070     Document Type: Article
Times cited : (71)

References (74)
  • 1
    • 7044235263 scopus 로고    scopus 로고
    • See for example: a) L. F. Tietze, Chem. Rev. 1996, 96, 115;
    • (1996) Chem. Rev. , vol.96 , pp. 115
    • Tietze, L.F.1
  • 12
    • 0001278542 scopus 로고
    • (Eds.: R. Adams, W. E. Bachmann, L. F. Fieser, J. R. Johnson, H. R. Snyder), John Wiley, New York
    • b) C. Djerassi, in: Org. React., vol. 6 (Eds.: R. Adams, W. E. Bachmann, L. F. Fieser, J. R. Johnson, H. R. Snyder), John Wiley, New York, 1953, pp. 207;
    • (1953) Org. React. , vol.6 , pp. 207
    • Djerassi, C.1
  • 13
    • 0000426886 scopus 로고
    • (Eds.: R. Adams, W. E. Bachmann, L. F. Fieser, J. R. Johnson, H. R. Snyder), John Wiley & Sons, New York
    • c) A. L. Wilds, in: Org. React., vol. 2 (Eds.: R. Adams, W. E. Bachmann, L. F. Fieser, J. R. Johnson, H. R. Snyder), John Wiley & Sons, New York, 1944, pp. 178.
    • (1944) Org. React. , vol.2 , pp. 178
    • Wilds, A.L.1
  • 14
    • 33845374137 scopus 로고
    • The literature contains very few reports of stoichiometric crossover transfer hydrogenation reactions between alcohols and alkenes. A few examples of crossover transfer hydrogenation using a small excess of alkene acceptor have been reported. See for example: M. E. Krafft, B. Zorc, J. Org. Chem. 1986, 51, 5482.
    • (1986) J. Org. Chem. , vol.51 , pp. 5482
    • Krafft, M.E.1    Zorc, B.2
  • 17
    • 0347485229 scopus 로고    scopus 로고
    • There are numerous reports of tandem oxidation-olefination reactions (2 of the 3 steps involved in our domino reaction sequence). See for example: a) L. Blackburn, R. J. K. Taylor, Synlett 2002, 215;
    • (2002) Synlett , pp. 215
    • Blackburn, L.1    Taylor, R.J.K.2
  • 47
    • 33749429245 scopus 로고    scopus 로고
    • note
    • Control experiments in the presence of excess alcohol exhibited no hydrogenolysis of the benzyl ester.
  • 56
    • 33749449542 scopus 로고    scopus 로고
    • note
    • The ultimate fate of carbon monoxide is unknown. Iridium carbonyl complexes are stable species thus it is plausible that this step represents a catalyst termination event.
  • 64
    • 33749442256 scopus 로고    scopus 로고
    • note
    • 3-methyl-2-buten-1-ol (not shown) afforded a complex reaction mixture from which none of the desired product could be isolated.
  • 65
    • 33749432218 scopus 로고    scopus 로고
    • note
    • Reactions with the cyano ylide 19 yielded mixtures of E/Z α,β-unsaturated nitriles, even under the thermodynamic conditions.
  • 71
    • 33749446149 scopus 로고    scopus 로고
    • note
    • This particular substrate proved troublesome to isolate both because of its volatility and the tendency for it to be destroyed under the oxidative workup conditions; identification of the product was therefore achieved by hydrogenation of the alkene present in the alkene/alkane mixture.
  • 72
    • 33749427277 scopus 로고    scopus 로고
    • note
    • Under the domino reaction conditions the olefination reaction is rapid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.