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Volumn 51, Issue 16, 2010, Pages 2168-2169

Enantioselective alkynylation of ketones with trimethoxysilylalkynes using lithium binaphtholate as a catalyst

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLPYRIDINE; ALKYNE DERIVATIVE; KETONE DERIVATIVE; LITHIUM BINAPHTHOLATE; LITHIUM DERIVATIVE; TRIMETHOXYSILYLALKYNE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77949489293     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.084     Document Type: Article
Times cited : (19)

References (39)
  • 3
    • 77949492747 scopus 로고    scopus 로고
    • note
    • The alkylation of ynones is a less reliable alternative method, because the unstable ynones are prone to decomposition or isomerization.
  • 4
  • 31
    • 0342302945 scopus 로고    scopus 로고
    • Lithium binaphtholate as a catalyst:
    • Lithium binaphtholate as a catalyst:. Schiffers R., and Kagan H.B. Synlett (1997) 1175
    • (1997) Synlett , pp. 1175
    • Schiffers, R.1    Kagan, H.B.2
  • 34
    • 77949491911 scopus 로고    scopus 로고
    • note
    • 3,3′-Dimethyl-, dichloro-, dibromobinaphthol, or mono lithium salt of the binaphthol derivatives gave lower yields and/or enantioselectivities.
  • 35
    • 77949487392 scopus 로고    scopus 로고
    • note
    • Representative experimental procedure: n-BuLi (0.16 M in hexane, 0.58 mL, 0.094 mmol) was added to a solution of (R)-3,3′-diphenylbinaphthol (21 mg, 0.047 mmol) in THF (3 mL) at 0 °C under Ar atmosphere. Trimethoxy-(phenylethynyl)silane (156 mg, 0.71 mmol) was added to the mixture in one portion, and then a solution of acetophenone (56 mg, 0.47 mmol) in THF (0.5 mL) was added over 3 h at the same temperature. After stirring for another 1 h, the reaction was quenched with tetrabutylammonium fluoride (1.0 M in THF, 4 mL). The mixture was stirred for 0.5 h and extracted with EtOAc. The organic layer was washed with water and brine successively. Drying over sodium sulfate and concentration followed by silica gel column chromatography afforded the alcohol (67 mg, 64%) as a colorless oil.
  • 38
    • 77949485391 scopus 로고    scopus 로고
    • note
    • The only reported example for the phenylalkynylation of acetylpyridine shows an unsatisfactory result (28% yield, 28% ee), see Ref. 6c.
  • 39
    • 77949488318 scopus 로고    scopus 로고
    • note
    • 3-Phenyl-1-(3-pyridyl)-2-propyn-1-ol has an antifungal activity, see Ref. 17a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.