A highly stereoselective synthesis of a key intermediate of 1β-methylcarbapenems employing the reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives |
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Authors: | Yoshio Ito Shiro Terashima |
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Affiliation: | Sagami Chemical Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229, Japan |
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Abstract: | Reaction of sterically crowded achiral 3-(2-bromopropionyl)-2-oxazolidone derivatives with (3,4)-4-acetoxy-3-[()-1-(-butyldimethylsilyloxy)ethyl]-2-azetidinone in the presence of zinc dust in refluxing tetrahydrofuran was found to give the 1β-methyl substituted β-lactams as major products (at most, β:=95:5). The major products were readily converted into the key intermediate of 1β-methylcarbapenems. |
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