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0032499051
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Rahim M.A., Taguchi H., Watanabe M., Fujiwara T., Takeda T. Tetrahedron Lett. 39:1998;2153.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 2153
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Rahim, M.A.1
Taguchi, H.2
Watanabe, M.3
Fujiwara, T.4
Takeda, T.5
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0036970697
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Takeda T., Shimane K., Ito K., Saeki N., Tsubouchi A. Chem. Commun. 2002;1974.
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(2002)
Chem. Commun.
, pp. 1974
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Takeda, T.1
Shimane, K.2
Ito, K.3
Saeki, N.4
Tsubouchi, A.5
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12
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0000387189
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Connor D.S., Klein G.W., Taylor G.N., Boeckman R.K. Jr., Medwid J.B. Org. Synth., Coll. VI. 1988;101.
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(1988)
Org. Synth., Coll. VI
, pp. 101
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Connor, D.S.1
Klein, G.W.2
Taylor, G.N.3
Boeckman R.K., Jr.4
Medwid, J.B.5
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13
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85031055078
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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.
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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.
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15
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85031062918
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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.
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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.
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16
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85031065653
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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
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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.
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17
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85031063171
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2: 3=4.5:4.5:9:1:4. The products could be isolated by silica gel PTLC without any precaution
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3: 2 : 3 =4.5:4.5:9:1:4. The products could be isolated by silica gel PTLC without any precaution.
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18
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85031053014
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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
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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.
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19
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85031063458
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4c,j-m was determined by NOE experiment.
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Configuration of the trisubstituted olefins 4c,j-m was determined by NOE experiment.
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