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Volumn 44, Issue 43, 2003, Pages 7897-7900

Preparation of enol ethers by carbonyl olefination utilizing an alkoxymethyl chloride-titanocene(II) system

Author keywords

Carbonyl compounds; Enol ethers; Olefination; Titanium and compounds

Indexed keywords

ALDEHYDE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; ESTER; ETHER DERIVATIVE; KETONE; LACTONE; METHYL GROUP; TITANIUM DERIVATIVE; TITANOCENE;

EID: 0141596923     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.013     Document Type: Article
Times cited : (13)

References (24)
  • 13
    • 85031055078 scopus 로고    scopus 로고
    • The present alkoxymethylenation of the aromatic aldehydes such as benzaldehyde and 1-naphthaldehyde resulted in the formation of complex mixtures and the olefination products were obtained in poor yields.
    • The present alkoxymethylenation of the aromatic aldehydes such as benzaldehyde and 1-naphthaldehyde resulted in the formation of complex mixtures and the olefination products were obtained in poor yields.
  • 15
    • 85031062918 scopus 로고    scopus 로고
    • 3 (6.0 mmol), and the mixture was stirred for 20 min. The mixture was warmed up to -10°C and a THF (1 mL) solution of 2a (119 mg, 0. 50 mmol) was added over 10 min. After stirring for 3 h, the reaction was quenched by addition of 1 M NaOH. The usual work-up and purification gave 88 mg of 4i in 66% yield.
    • 3 (6.0 mmol), and the mixture was stirred for 20 min. The mixture was warmed up to -10°C and a THF (1 mL) solution of 2a (119 mg, 0.50 mmol) was added over 10 min. After stirring for 3 h, the reaction was quenched by addition of 1 M NaOH. The usual work-up and purification gave 88 mg of 4i in 66% yield.
  • 16
    • 85031065653 scopus 로고    scopus 로고
    • 3e and the dichloride 5 gave 1-(1-methyl-2-methoxyethenyl)naphthalene in 44 and 54% yields, respectively. Almost identical stereoselectivity (E:Z=70: 30 for 3e, 72: 28 for 5) suggested that both reactions proceed through the formation of the same active intermediate
    • The methoxymethylenations of methyl 1-naphthyl ketone with the monochloride 3e and the dichloride 5 gave 1-(1-methyl-2-methoxyethenyl)naphthalene in 44 and 54% yields, respectively. Almost identical stereoselectivity (E:Z=70: 30 for 3e , 72: 28 for 5 ) suggested that both reactions proceed through the formation of the same active intermediate.
  • 17
    • 85031063171 scopus 로고    scopus 로고
    • 2: 3=4.5:4.5:9:1:4. The products could be isolated by silica gel PTLC without any precaution
    • 3: 2 : 3 =4.5:4.5:9:1:4. The products could be isolated by silica gel PTLC without any precaution.
  • 18
    • 85031053014 scopus 로고    scopus 로고
    • 2a with 3a, the formation of phenethyl methyl ether in an amount corresponding to the olefination product 4f was observed, supporting the reaction path depicted in Scheme 2
    • In the alkoxymethylenation of 2a with 3a , the formation of phenethyl methyl ether in an amount corresponding to the olefination product 4f was observed, supporting the reaction path depicted in Scheme 2.
  • 19
    • 85031063458 scopus 로고    scopus 로고
    • 4c,j-m was determined by NOE experiment.
    • Configuration of the trisubstituted olefins 4c,j-m was determined by NOE experiment.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.