Catalytic Cyclopropanation of Ricinolic Acid Derivatives with Diazomethane |
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| Authors: | A M Davletbakova I O Maidanova N Z Baibulatova V A Dokichev Yu V Tomilov M S Yunusov and O M Nefedov |
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| Institution: | (1) Ufa Research Center, Russian Academy of Sciences, Institute of Organic Chemistry, pr. Oktyabrya 71, Ufa, 450054 Bashkortostan, Russia;(2) Russian Academy of Sciences, Zelinskii Institute of Organic Chemistry, Moscow, Russia |
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| Abstract: | The reaction of ricinolic acid methyl ester with diazomethane in the presence of Co(BF4)2·6H2Oresults in selective methylation of the hydroxy group. Methyl (2Z'12R)-12-acetoxy-9-octadecenoate reactswith diazomethane in the presence of Pd(acac)2, leading to formation of a mixture of cis-cyclopropanated(9S'10S'12R)-, (9R'10R'12R)-diastereoisomers at a ratio of 3:2 (overall yield 73%). Under similarconditions methyl (9Z)-12-oxo-9-octadecenoate gives rise to optically inactive methyl cis-8-2-(2-oxooctyl)-cyclopropyl]octanoate. |
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