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Volumn 76, Issue 5, 2011, Pages 1479-1482

A general procedure for the synthesis of enones via gold-catalyzed Meyer-Schuster rearrangement of propargylic alcohols at room temperature

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID; HIGH SELECTIVITY; MEYER-SCHUSTER REARRANGEMENT; ONE-POT PROCEDURES; PROPARGYLIC ALCOHOLS; ROOM TEMPERATURE; TERTIARY ALCOHOLS;

EID: 79952134855     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102263t     Document Type: Article
Times cited : (94)

References (47)
  • 9
    • 77749327971 scopus 로고    scopus 로고
    • For recent reviews on gold catalysis, see:;,-691
    • For recent reviews on gold catalysis, see: Shapiro, N. D.; Toste, F. D. Synlett 2010, 675-691
    • (2010) Synlett , pp. 675
    • Shapiro, N.D.1    Toste, F.D.2
  • 12
  • 15
    • 51249100498 scopus 로고    scopus 로고
    • Arcadi, A. Chem. Rev. 2008, 108, 3266-3325
    • (2008) Chem. Rev. , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 36
    • 34250636379 scopus 로고    scopus 로고
    • For examples of other metal catalysts for the Meyer-Schuster rearrangement, see:;;,-2699
    • For examples of other metal catalysts for the Meyer-Schuster rearrangement, see: Tanaka, K.; Shoji, T.; Hirano, M. Eur. J. Org. Chem. 2007, 2687-2699
    • (2007) Eur. J. Org. Chem. , pp. 2687
    • Tanaka, K.1    Shoji, T.2    Hirano, M.3
  • 41
    • 79952182293 scopus 로고    scopus 로고
    • We have observed that commercially available samples of phenylboronic acid often contain large quantities of the trimeric boroxine and this may account for its poor reactivity in this reaction.
    • We have observed that commercially available samples of phenylboronic acid often contain large quantities of the trimeric boroxine and this may account for its poor reactivity in this reaction.
  • 44
    • 0000763824 scopus 로고
    • See also ref 7a for a synthesis of this compound via a gold-catalyzed Meyer-Schuster rearrangement that proceeds with much lower E: Z selectivity
    • Bunnelle, W. H.; Rafferty, M. A.; Hodges, S. L. J. Org. Chem. 1987, 52, 1603-1605 See also ref 7a for a synthesis of this compound via a gold-catalyzed Meyer-Schuster rearrangement that proceeds with much lower E: Z selectivity.
    • (1987) J. Org. Chem. , vol.52 , pp. 1603-1605
    • Bunnelle, W.H.1    Rafferty, M.A.2    Hodges, S.L.3
  • 45
    • 79952173458 scopus 로고    scopus 로고
    • The addition of methanol to unsubstituted enones during Au(I)-catalyzed Meyer-Schuster rearrangements has been previously observed, see ref 6.
    • The addition of methanol to unsubstituted enones during Au(I)-catalyzed Meyer-Schuster rearrangements has been previously observed, see ref 6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.