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Volumn 2, Issue 7, 2011, Pages 1305-1310

Mild and selective boronic acid catalyzed 1,3-transposition of allylic alcohols and Meyer-Schuster rearrangement of propargylic alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; BORONIC ACID; CARBOCATIONS; ELECTRON-DEFICIENT; METAL-FREE CONDITIONS; MEYER-SCHUSTER REARRANGEMENT; PROPARGYLIC ALCOHOLS; TANDEM REACTION;

EID: 79959486571     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c1sc00140j     Document Type: Article
Times cited : (100)

References (75)
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    • Concepts of Modern Catalysis and Kinetics 2nd and Completely Revised and Enlarged Edition, Ed, Chorkendorff and J. W. Niemantsverdriet, Wiley-VCH, Weinheim
    • Concepts of Modern Catalysis and Kinetics: 2nd and Completely Revised and Enlarged Edition, ed. I. Chorkendorff and J. W. Niemantsverdriet, Wiley-VCH, Weinheim, 2007.
    • (2007)
  • 21
    • 79959449338 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
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    • For reviews, see
    • For reviews, see
  • 27
    • 77950896030 scopus 로고    scopus 로고
    • For recent references on the Meyer-Schuster rearrangement of propargylic alcohols, see
    • V. Cadierno, P. Crochet, D. E. Garcia-Garrido and J. Gimeno, Dalton Trans., 2010, 39, 4015-4031. For recent references on the Meyer-Schuster rearrangement of propargylic alcohols, see
    • (2010) Dalton Trans , vol.39 , pp. 4015-4031
    • Cadierno, V.1    Crochet, P.2    Garcia-Garrido, D.E.3    Gimeno, J.4
  • 33
  • 41
    • 79959455889 scopus 로고    scopus 로고
    • For recent references on the 1,3-transposition of allylic esters, silyl ethers, ortho esters, and others, see
    • For recent references on the 1,3-transposition of allylic esters, silyl ethers, ortho esters, and others, see
  • 43
  • 54
    • 79959397136 scopus 로고    scopus 로고
    • For selected and recent examples with allylic alcohols
    • For selected and recent examples with allylic alcohols
  • 66
    • 79959383801 scopus 로고    scopus 로고
    • Additives tried without success: TsOH (20 mol%) and ZrCl4 (20 mol%)
    • Additives tried without success: TsOH (20 mol%) and ZrCl4 (20 mol%).
  • 67
    • 79959385676 scopus 로고    scopus 로고
    • Use of optimal O3ReOSiPh3 catalyzed conditions provided the following outcome (yield (%) (E: Z)): entry 8: 71 (5: 1); entry 9: 63 (1: 3.5); entry 10: 85 (5: 1); entry 11: 81 (3: 1). Use of AuCl3 catalyzed conditions for entry 25: 92%, 10: 1 E: Z. Au catalysis (AuCl3) failed with allylic alcohol 1a. Re catalysis failed with allylic alcohol 2k, and propargylic alcohols 4a and 4c. See ESI† for more details
    • Use of optimal O3ReOSiPh3 catalyzed conditions provided the following outcome (yield (%) (E: Z)): entry 8: 71 (5: 1); entry 9: 63 (1: 3.5); entry 10: 85 (5: 1); entry 11: 81 (3: 1). Use of AuCl3 catalyzed conditions for entry 25: 92%, 10: 1 E: Z. Au catalysis (AuCl3) failed with allylic alcohol 1a. Re catalysis failed with allylic alcohol 2k, and propargylic alcohols 4a and 4c. See ESI† for more details.
  • 68
    • 79959388782 scopus 로고    scopus 로고
    • After completion of a reaction with substrate 2e (24 h) under optimized reaction conditions (Table 2), an additional equal amount of starting material 2e was added to the reaction mixture. Upon stirring for another 24 h, the reaction gave the desired product 3e in the same yield (80%). See ESI† for more details
    • After completion of a reaction with substrate 2e (24 h) under optimized reaction conditions (Table 2), an additional equal amount of starting material 2e was added to the reaction mixture. Upon stirring for another 24 h, the reaction gave the desired product 3e in the same yield (80%). See ESI† for more details
  • 69
    • 79959417109 scopus 로고    scopus 로고
    • For a related, original discussion of similar mechanisms using metaloxo catalysts, see
    • For a related, original discussion of similar mechanisms using metaloxo catalysts, see
  • 71
    • 79959389353 scopus 로고    scopus 로고
    • Protic acid catalysis can be ruled out based on the weak acidity of boronic acids and an unsuccessful attempt to catalyze the reaction of 2a with TsOH$H2O under the same conditions as Table 2, entry 1
    • Protic acid catalysis can be ruled out based on the weak acidity of boronic acids and an unsuccessful attempt to catalyze the reaction of 2a with TsOH$H2O under the same conditions as Table 2, entry 1.
  • 72
    • 79959482788 scopus 로고    scopus 로고
    • See ESI† for more details
    • See ESI† for more details.
  • 73
    • 79959427762 scopus 로고    scopus 로고
    • For similar examples, see
    • For similar examples, see


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.