메뉴 건너뛰기




Volumn 16, Issue 38, 2010, Pages 11567-11571

A tetranuclear-zinc-cluster-catalyzed practical and versatile deprotection of acetates and benzoates

Author keywords

Cluster compounds; Deacylation; Homogeneous catalysis; Transesterification; Zinc

Indexed keywords

CATALYTIC AMOUNTS; CLUSTER COMPOUNDS; DEACYLATION; DEPROTECTION; HOMOGENEOUS CATALYSIS; ZINC CLUSTERS;

EID: 77957582085     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000960     Document Type: Article
Times cited : (39)

References (47)
  • 2
    • 0003417469 scopus 로고
    • Eds.: B. M. Trost, I. Fleming, Pergamon Press, New York
    • a) J. Mulzer in Comprehensive Organic Synthesis, Vol. 6 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1992;
    • (1992) Comprehensive Organic Synthesis , vol.6
    • Mulzer, J.1
  • 7
    • 0003768632 scopus 로고    scopus 로고
    • For a general review, see:, Eds.: P. T. Anastas, T. C. Williamson, Oxford University Press, Oxford
    • For a general review, see: Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes (Eds.: P. T. Anastas, T. C. Williamson), Oxford University Press, Oxford, 1998.
    • (1998) Green Chemistry: Frontiers in Benign Chemical Syntheses and Processes
  • 8
    • 0001595852 scopus 로고
    • For reviews, see: a
    • For reviews, see: a) J. Otera, Chem. Rev. 1993, 93, 1449;
    • (1993) Chem. Rev. , vol.93 , pp. 1449
    • Otera, J.1
  • 29
    • 84874217580 scopus 로고    scopus 로고
    • It is reported that deacetylation of propargylic tertiary acetates is exceptionally high as compared with other tertiary acetates
    • It is reported that deacetylation of propargylic tertiary acetates is exceptionally high as compared with other tertiary acetates.
  • 34
    • 84874204628 scopus 로고    scopus 로고
    • The Zn cluster 1 is marketed as ZnTAC24 from STREM produced by Takasago International corp., Japan
    • The Zn cluster 1 is marketed as ZnTAC24 from STREM (produced by Takasago International corp., Japan).
  • 39
    • 17444395097 scopus 로고    scopus 로고
    • For a general review, see: a, Eds.: M. Shibasaki, Y Yamamoto, Wiley-VCH, Weinheim, for representative examples of multinuclear zinc catalysts, see
    • For a general review, see: a) Multimetallic Catalysts in Organic Synthesis (Eds.: M. Shibasaki, Y Yamamoto), Wiley-VCH, Weinheim, 2004; for representative examples of multinuclear zinc catalysts, see
    • (2004) Multimetallic Catalysts in Organic Synthesis
  • 42
    • 84874214044 scopus 로고    scopus 로고
    • Although both MeOH and EtOH gave nearly the same results, we set MeOH rather than EtOH as the standard nucleophile because of larger boiling temperature difference between nucleophile and coproduct ester MeOH: 64.5°C, MeOAc: 57-58°C, DT ≈ 7°C; EtOH: 78.3°C, EtOAc: 77.1 °C, ΔT=1.2°C
    • Although both MeOH and EtOH gave nearly the same results, we set MeOH rather than EtOH as the standard nucleophile because of larger boiling temperature difference between nucleophile and coproduct ester (MeOH: 64.5°C, MeOAc: 57-58°C, DT ≈ 7°C; EtOH: 78.3°C, EtOAc: 77.1 °C, ΔT=1.2°C).
  • 45
    • 84874212615 scopus 로고    scopus 로고
    • 18 the Zn cluster showed comparable catalyst activity in various solvents, including hexane, toluene, chlorobenzene, diglyme, dioxane, DMF, and DMSO. Thus, in the case of substrates that are insoluble in alcohols, mix-solvent system would be a good choice of solvents. For example, the deacetylation of 2a 1.0 mmol in MeOH/hexane 1:1, 2 mL gave 3a in 89% yield
    • [18] the Zn cluster showed comparable catalyst activity in various solvents, including hexane, toluene, chlorobenzene, diglyme, dioxane, DMF, and DMSO. Thus, in the case of substrates that are insoluble in alcohols, mix-solvent system would be a good choice of solvents. For example, the deacetylation of 2a (1.0 mmol) in MeOH/hexane (1:1, 2 mL) gave 3a in 89% yield.
  • 46
    • 84874214741 scopus 로고    scopus 로고
    • 10c, 14
    • [10c, 14]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.