Mild and efficient synthesis of (Z)-alpha-chloroalkylidene-beta-lactones via the PdCl2-catalyzed cyclocarbonylation of 2-alkynols |
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| Authors: | Ma Shengming Wu Bin Zhao Shimin |
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| Institution: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China. masm@mail.sioc.ac.cn |
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| Abstract: | reaction: see text] A mild and efficient methodology involving PdCl(2)-catalyzed cyclocarbonylation of 2-alkynols with CuCl(2) for the synthesis of (Z)-alpha-chloroalkylidene-beta-lactones was developed. Using the readily available optically active propargylic alcohols allows convenient synthesis of the corresponding (Z)-alpha-chloroalkylidene-beta-lactones with high ee values. cis-Chloropalladation was observed as the major pathway, which is unique as compared to the reported data. |
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