Art

J-GLOBAL ID：200902111333868839   Reference number：00A0234687

A Direct and Selective Syntheses of α,α-Dichloro- and α-Chloro-ethyl Ketones by the Reaction of Alkyl Carboxylates with 1,1-Dichloroethyllithium.

カルボン酸アルキルと1,1-ジクロロエチルリチウムの反応によるα,α-ジクロロ-及びα-クロロエチルケトンの直接かつ選択的合成

Author (4)： SHIINA I (Sci. Univ. Tokyo, Tokyo) ,  IMAI Y (Sci. Univ. Tokyo, Tokyo) ,  KAGAYAMA A (Sci. Univ. Tokyo, Tokyo) ,  MUKAIYAMA T (Sci. Univ. Tokyo, Tokyo)
Material： Chemistry Letters  (Chem Lett)
Issue： 2  Page： 190-191  Publication year： Feb. 05, 2000 
JST Material Number： S0742A  ISSN： 0366-7022  CODEN： CMLTAG  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： chemical synthesis ,...
Semi thesaurus term： bridged compound

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JST classification (1)： Aromatic monocyclic ketones  (CF05170I)

Substance index (23)： Paclitaxel ,  (4R,5R,7R,8S)-2,2-Dichloro-4,8-bis(benzyloxy)-5,9-bis(tert-butyldimethylsiloxy)-6,6-dimethyl-7-(4-methoxybenzyloxy)-3-nonanone ,  (4R,5R,7R,8S)-2-Chloro-4,8-bis(benzyloxy)-5,9-bis(tert-butyldimethylsiloxy)-6,6-dimethyl-7-(4-methoxybenzyloxy)-3-nonanone ,  1,1-Dichloro-1-lithioethane ,  1,1-Dichloroethane ,  2-Methyl-3-phenylpropanoic acid ethyl ester ,  α,α-Dimethylbenzenepropionic acid ethyl ester ,  (2S,3S)-2-Methyl-3-(tert-butyldimethylsiloxy)-3-phenylpropionic acid ethyl ester ,  (2R,3S)-2-Methyl-3-(tert-butyldimethylsiloxy)-3-phenylpropionic acid ethyl ester ,  (2S,3R)-2-(Benzyloxy)-3-(tert-butyldimethylsiloxy)-3-phenylpropionic acid methyl ester ,  (2R,3R)-2-(Benzyloxy)-3-(tert-butyldimethylsiloxy)-3-phenylpropionic acid methyl ester ,  1-Phenyl-2-methyl-4,4-dichloro-3-pentanone ,  1-Phenyl-2-methyl-4-chloro-3-pentanone ,  1-Phenyl-2,2-dimethyl-4,4-dichloro-3-pentanone ,  1-Phenyl-2,2-dimethyl-4-chloro-3-pentanone ,  (1S,2S)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-methyl-4,4-dichloro-3-pentanone ,  (1S,2S)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-methyl-4-chloro-3-pentanone ,  (1S,2R)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-methyl-4,4-dichloro-3-pentanone ,  (1S,2R)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-methyl-4-chloro-3-pentanone ,  (1R,2S)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-(benzyloxy)-4,4-dichloro-3-pentanone ,  (1R,2S)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-(benzyloxy)-4-chloro-3-pentanone ,  (1R,2R)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-(benzyloxy)-4,4-dichloro-3-pentanone ,  (1R,2R)-1-Phenyl-1-(tert-butyldimethylsiloxy)-2-(benzyloxy)-4-chloro-3-pentanone

Reference (16)：

• 1) T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada, and K. Saitoh, Chem. Eur. J., 5, 121 (1999), and references cited therein;
•  H. Iwadare, H. Sakoh, H. Arai, I. Shiina, and T. Mukaiyama, Chem. Lett., 1999, 817.
• 2) I. Shiina, J. Shibata, Y. Imai, R. Ibuka, H. Fujisawa, I. Hachiya, and T. Mukaiyama, Chem. Lett., 1999, 1145.
• 3) For a review, see: G. Cainelli, A. U. Ronchi, F. Bertini, P. Grasselli, and G. Zubiani, Tetrahedron, 27, 6109 (1971);
•  G. Köbrich, Angew. Chem., Int. Ed. Engl., 11, 473 (1972).

Terms in the title (1)： カルボン酸