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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 4
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Original Articles

Improved Ozonolysis Mediated by Metal Chlorides

Koichi Tsuji Microbiological Research Institute, Otsuka Pharmaceutical Co. Ltd., Kagasuno 463-10, Kawauchi-cho, Tokushima, 771-01, Japan
&
Hiroshi Ishikawa Microbiological Research Institute, Otsuka Pharmaceutical Co. Ltd., Kagasuno 463-10, Kawauchi-cho, Tokushima, 771-01, Japan
Pages 595-600 | Received 29 Jul 1996, Published online: 20 Aug 2006
 
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Abstract

The styrylazetidinones 3a, b, the intermediates of novel 2-oxaisocephems, were ozonolyzed at −10∼3°C effectively and safely in the presence of 0.1 equiv of some metal chlorides to afford diols 4a, b after reduction by NaBH4-BF3·Et2O in the same yield as ozonolysis at −50°C.

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